New syntheses of d-tagatose and of 1,5-anhydro- d-tagatose from d-galactose derivatives
3,4- O-Isopropylidene- d- lyxo-hexopyranosid-2-ulose derivatives, obtained by oxidation of 3,4,6-protected d-galactopyranosides, can be alkylated in their anionic 2,6-pyranose forms to produce bis-glycosides containing the 2,5-dioxabicyclo[2.2.2]octane ring system. The 1-benzyl-2-methyl bis-glycosid...
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| Published in: | Carbohydrate research Vol. 274; pp. 197 - 208 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
08-09-1995
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| Abstract | 3,4-
O-Isopropylidene-
d-
lyxo-hexopyranosid-2-ulose derivatives, obtained by oxidation of 3,4,6-protected
d-galactopyranosides, can be alkylated in their anionic 2,6-pyranose forms to produce bis-glycosides containing the 2,5-dioxabicyclo[2.2.2]octane ring system. The 1-benzyl-2-methyl bis-glycoside
4b, when subjected to catalytic hydrogenolysis, produces the methyl
d-
lyxo-hexopyranos-2-uloside
10, existing as an 8:2 mixture of 1,5-pyranose anomers
9. Computational and NMR evidence is presented in favour of the hypothesis that the major anomer has the α configuration. Reduction of
9/10 with NaBH
4 gives methyl 3,4-
O-isopropylidene-β-
d-tagatopyranoside, that can be hydrolyzed to
d-tagatose. A simple synthesis of 1,5-anhydro-
d-tagatose, starting from 1,5-anhydro-
d-galactitol, is also presented. All new compounds were fully characterized by elemental analysis and by
1H and
13C NMR spectroscopy. |
|---|---|
| AbstractList | 3,4-
O-Isopropylidene-
d-
lyxo-hexopyranosid-2-ulose derivatives, obtained by oxidation of 3,4,6-protected
d-galactopyranosides, can be alkylated in their anionic 2,6-pyranose forms to produce bis-glycosides containing the 2,5-dioxabicyclo[2.2.2]octane ring system. The 1-benzyl-2-methyl bis-glycoside
4b, when subjected to catalytic hydrogenolysis, produces the methyl
d-
lyxo-hexopyranos-2-uloside
10, existing as an 8:2 mixture of 1,5-pyranose anomers
9. Computational and NMR evidence is presented in favour of the hypothesis that the major anomer has the α configuration. Reduction of
9/10 with NaBH
4 gives methyl 3,4-
O-isopropylidene-β-
d-tagatopyranoside, that can be hydrolyzed to
d-tagatose. A simple synthesis of 1,5-anhydro-
d-tagatose, starting from 1,5-anhydro-
d-galactitol, is also presented. All new compounds were fully characterized by elemental analysis and by
1H and
13C NMR spectroscopy. 3,4-O-Isopropylidene-D-lyxo-hexopyranosid-2-ulose derivatives, obtained by oxidation of 3,4,6-protected D-galactopyranosides, can be alkylated in their anionic 2,6-pyranose forms to produce bis-glycosides containing the 2,5-dioxabicyclo[2.2.2]octane ring system. The 1-benzyl-2-methyl bis-glycoside 4b, when subjected to catalytic hydrogenolysis, produces the methyl D-lyxo-hexopyranos-2-uloside 10, existing as an 8:2 mixture of 1,5-pyranose anomers 9. Computational and NMR evidence is presented in favour of the hypothesis that the major anomer has the alpha configuration. Reduction of 9/10 with NaBH4 gives methyl 3,4-O-isopropylidene-beta-D-tagatopyranoside, that can be hydrolyzed to D-tagatose. A simple synthesis of 1,5-anhydro-D-tagatose, starting from 1,5-anhydro-D-galactitol, is also presented. All new compounds were fully characterized by elemental analysis and by 1H and 13C NMR spectroscopy. |
| Author | Berti, Giancarlo Barili, Pier Luigi D'Andrea, Felicia Catelani, Giorgio Miarelli, Lucia |
| Author_xml | – sequence: 1 givenname: Pier Luigi surname: Barili fullname: Barili, Pier Luigi – sequence: 2 givenname: Giancarlo surname: Berti fullname: Berti, Giancarlo – sequence: 3 givenname: Giorgio surname: Catelani fullname: Catelani, Giorgio – sequence: 4 givenname: Felicia surname: D'Andrea fullname: D'Andrea, Felicia – sequence: 5 givenname: Lucia surname: Miarelli fullname: Miarelli, Lucia |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/7585706$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1002_hlca_200390083 crossref_primary_10_1080_07328309708005733 crossref_primary_10_1002_chin_199602271 crossref_primary_10_1016_j_carres_2006_03_001 crossref_primary_10_1021_acscatal_9b01339 crossref_primary_10_1021_jf203897a crossref_primary_10_1016_j_tetasy_2009_03_016 crossref_primary_10_1016_S0008_6215_98_00058_5 crossref_primary_10_1016_0008_6215_96_00121_8 crossref_primary_10_1016_j_carres_2021_108377 crossref_primary_10_1016_S0040_4039_02_00118_1 crossref_primary_10_1002_ejoc_201300935 |
| Cites_doi | 10.1016/S0040-4039(00)84515-3 10.1016/0003-9861(88)90566-8 10.1016/S0031-9422(00)81819-1 10.1038/163177b0 10.1002/cber.19771101008 10.1002/cber.19791120637 10.1002/recl.18970160902 10.1016/S0040-4039(00)92737-0 10.1016/S0021-9258(18)43564-8 10.1016/0008-6215(89)84142-4 10.1016/S0040-4039(00)92130-0 10.1016/S0040-4039(00)60933-4 10.1002/cber.19671000738 10.1016/S0040-4020(01)87843-1 10.1039/c39870001625 10.1002/hlca.19340170194 10.1055/s-1981-29377 10.1016/S0040-4020(01)88219-3 10.1021/ja01177a037 10.1002/cber.19801131225 10.1002/cber.19791120636 10.1016/0008-6215(91)84075-P |
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| Keywords | β- d-Tagatopyranoside d-Tagatose 1,5-Anhydro- d-tagatose 2,5-Dioxabicyclo[2.2.2]octane |
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| References | Köll, Tayman (BIB14) 1977; 110 Wehrli, Wirthlin (BIB19) 1976 Mancuso, Swern (BIB12) 1981 Barili, Berti, Catelani, D'Andrea, Barili, Berti, Catelani, D'Andrea (BIB2) 1991; 32 Köll, Tayman (BIB16) 1979; 112 Barili, Berti, Catelani, Colonna, Marra (BIB10) 1986; 27 Totton, Lardy (BIB25) 1949; 71 Bissett, Anderson (BIB7) 1980; 255 Reichstein, Bosshard (BIB24) 1934; 17 Barili, Berti, D'Andrea, Di Bussolo, Granucci (BIB3) 1992; 48 Lichtenthaler, El Ashry, Göckel (BIB22) 1980; 21 Köll, Tayman, Heyns (BIB17) 1979; 112 Barili, Berti, Catelani, D'Andrea, Gaudiosi, Barili, Berti, Catelani, D'Andrea, Gaudiosi (BIB4) 1991; 212 Griffith, Ley, Whitcombe, White (BIB20) 1987 Lobry de Bruyn, Alberda von Ekenstein (BIB5) 1897; 16 Barili, Berti, Bertozzi, Catelani, Colonna, Corsetti, D'Andrea (BIB23) 1990; 46 Barili, Berti, D'Andrea, Di Bussolo, Gaudiosi (BIB11) 1992; 33 Ciudad, Carabaza, Bosch, Gomez, Foix, Guinovart (BIB8) 1988; 264 Serena Software, P.O. Box 3076, Bloomington, IN 47402, USA, 1990. Micheel, Neier, Riedel (BIB13) 1967; 100 Zehner (BIB9) 1988; 109 Hirst, Hough, Jones (BIB6) 1949; 163 Köll, Komander, Kopf (BIB15) 1980; 113 Barili, Berti, Catelani, Colonna, D'Andrea (BIB1) 1989; 190 Deffieux, Baute, Baute, Atfani, Carpy (BIB21) 1987; 26 Köll (10.1016/0008-6215(95)00125-D_BIB14) 1977; 110 Bissett (10.1016/0008-6215(95)00125-D_BIB7) 1980; 255 Barili (10.1016/0008-6215(95)00125-D_BIB4_1) 1991; 212 Barili (10.1016/0008-6215(95)00125-D_BIB1) 1989; 190 Wehrli (10.1016/0008-6215(95)00125-D_BIB19) 1976 Barili (10.1016/0008-6215(95)00125-D_BIB23) 1990; 46 Zehner (10.1016/0008-6215(95)00125-D_BIB9) 1988; 109 Griffith (10.1016/0008-6215(95)00125-D_BIB20) 1987 Micheel (10.1016/0008-6215(95)00125-D_BIB13) 1967; 100 Barili (10.1016/0008-6215(95)00125-D_BIB2_2) 1992; 122 Barili (10.1016/0008-6215(95)00125-D_BIB10) 1986; 27 Totton (10.1016/0008-6215(95)00125-D_BIB25) 1949; 71 Ciudad (10.1016/0008-6215(95)00125-D_BIB8) 1988; 264 Reichstein (10.1016/0008-6215(95)00125-D_BIB24) 1934; 17 Lobry de Bruyn (10.1016/0008-6215(95)00125-D_BIB5) 1897; 16 Barili (10.1016/0008-6215(95)00125-D_BIB2_1) 1991; 32 Köll (10.1016/0008-6215(95)00125-D_BIB15) 1980; 113 Hirst (10.1016/0008-6215(95)00125-D_BIB6) 1949; 163 Mancuso (10.1016/0008-6215(95)00125-D_BIB12) 1981 Köll (10.1016/0008-6215(95)00125-D_BIB17) 1979; 112 10.1016/0008-6215(95)00125-D_BIB18 Barili (10.1016/0008-6215(95)00125-D_BIB3) 1992; 48 Lichtenthaler (10.1016/0008-6215(95)00125-D_BIB22) 1980; 21 Köll (10.1016/0008-6215(95)00125-D_BIB16) 1979; 112 Barili (10.1016/0008-6215(95)00125-D_BIB11) 1992; 33 Deffieux (10.1016/0008-6215(95)00125-D_BIB21) 1987; 26 Barili (10.1016/0008-6215(95)00125-D_BIB4_2) 1994; 124 |
| References_xml | – volume: 16 start-page: 262 year: 1897 end-page: 273 ident: BIB5 publication-title: Recl. Trav. Chim. contributor: fullname: Alberda von Ekenstein – volume: 21 start-page: 1429 year: 1980 end-page: 1432 ident: BIB22 publication-title: Tetrahedron Lett. contributor: fullname: Göckel – volume: 190 start-page: 13 year: 1989 end-page: 21 ident: BIB1 publication-title: Carbohydr. Res. contributor: fullname: D'Andrea – volume: 110 start-page: 3297 year: 1977 end-page: 3303 ident: BIB14 publication-title: Chem. Ber. contributor: fullname: Tayman – volume: 32 start-page: 959 year: 1991 end-page: 962 ident: BIB2 publication-title: Tetrahedron Lett. contributor: fullname: D'Andrea – volume: 71 start-page: 3076 year: 1949 end-page: 3078 ident: BIB25 publication-title: J. Am. Chem. Soc. contributor: fullname: Lardy – volume: 100 start-page: 2401 year: 1967 end-page: 2409 ident: BIB13 publication-title: Chem. Ber. contributor: fullname: Riedel – volume: 112 start-page: 2296 year: 1979 end-page: 2304 ident: BIB16 publication-title: Chem. Ber. contributor: fullname: Tayman – volume: 26 start-page: 1391 year: 1987 end-page: 1393 ident: BIB21 publication-title: Phytochemistry contributor: fullname: Carpy – volume: 113 start-page: 3919 year: 1980 end-page: 3926 ident: BIB15 publication-title: Chem. Ber. contributor: fullname: Kopf – start-page: 37 year: 1976 end-page: 39 ident: BIB19 article-title: Interpretation of Carbon-13 NMR Spectra contributor: fullname: Wirthlin – volume: 46 start-page: 5365 year: 1990 end-page: 5376 ident: BIB23 publication-title: Tetrahedron contributor: fullname: D'Andrea – volume: 255 start-page: 8750 year: 1980 end-page: 8755 ident: BIB7 publication-title: J. Biol. Chem. contributor: fullname: Anderson – start-page: 1625 year: 1987 end-page: 1627 ident: BIB20 publication-title: J. Chem. Soc., Chem. Commun. contributor: fullname: White – volume: 48 start-page: 6273 year: 1992 end-page: 6284 ident: BIB3 publication-title: Tetrahedron contributor: fullname: Granucci – volume: 212 start-page: c5 year: 1991 end-page: c7 ident: BIB4 publication-title: Carbohydr. Res. contributor: fullname: Gaudiosi – volume: 109 start-page: 36888d year: 1988 ident: BIB9 publication-title: Chem. Abstr. contributor: fullname: Zehner – volume: 27 start-page: 2307 year: 1986 end-page: 2310 ident: BIB10 publication-title: Tetrahedron Lett. contributor: fullname: Marra – volume: 264 start-page: 30 year: 1988 end-page: 39 ident: BIB8 publication-title: Arch. Biochem. Biophys. contributor: fullname: Guinovart – volume: 163 start-page: 177 year: 1949 ident: BIB6 publication-title: Nature (London) contributor: fullname: Jones – volume: 112 start-page: 2305 year: 1979 end-page: 2313 ident: BIB17 publication-title: Chem. Ber. contributor: fullname: Heyns – volume: 17 start-page: 753 year: 1934 end-page: 761 ident: BIB24 publication-title: Helv. Chim. Acta contributor: fullname: Bosshard – volume: 33 start-page: 7061 year: 1992 end-page: 7064 ident: BIB11 publication-title: Tetrahedron Lett. contributor: fullname: Gaudiosi – start-page: 165 year: 1981 end-page: 185 ident: BIB12 publication-title: Synthesis contributor: fullname: Swern – volume: 27 start-page: 2307 year: 1986 ident: 10.1016/0008-6215(95)00125-D_BIB10 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)84515-3 contributor: fullname: Barili – volume: 264 start-page: 30 year: 1988 ident: 10.1016/0008-6215(95)00125-D_BIB8 publication-title: Arch. Biochem. Biophys. doi: 10.1016/0003-9861(88)90566-8 contributor: fullname: Ciudad – start-page: 37 year: 1976 ident: 10.1016/0008-6215(95)00125-D_BIB19 article-title: Interpretation of Carbon-13 NMR Spectra contributor: fullname: Wehrli – volume: 26 start-page: 1391 year: 1987 ident: 10.1016/0008-6215(95)00125-D_BIB21 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)81819-1 contributor: fullname: Deffieux – volume: 163 start-page: 177 year: 1949 ident: 10.1016/0008-6215(95)00125-D_BIB6 publication-title: Nature (London) doi: 10.1038/163177b0 contributor: fullname: Hirst – volume: 110 start-page: 3297 year: 1977 ident: 10.1016/0008-6215(95)00125-D_BIB14 publication-title: Chem. Ber. doi: 10.1002/cber.19771101008 contributor: fullname: Köll – volume: 112 start-page: 2305 year: 1979 ident: 10.1016/0008-6215(95)00125-D_BIB17 publication-title: Chem. Ber. doi: 10.1002/cber.19791120637 contributor: fullname: Köll – volume: 16 start-page: 262 year: 1897 ident: 10.1016/0008-6215(95)00125-D_BIB5 publication-title: Recl. Trav. Chim. doi: 10.1002/recl.18970160902 contributor: fullname: Lobry de Bruyn – volume: 21 start-page: 1429 year: 1980 ident: 10.1016/0008-6215(95)00125-D_BIB22 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)92737-0 contributor: fullname: Lichtenthaler – volume: 255 start-page: 8750 year: 1980 ident: 10.1016/0008-6215(95)00125-D_BIB7 publication-title: J. Biol. Chem. doi: 10.1016/S0021-9258(18)43564-8 contributor: fullname: Bissett – volume: 190 start-page: 13 year: 1989 ident: 10.1016/0008-6215(95)00125-D_BIB1 publication-title: Carbohydr. Res. doi: 10.1016/0008-6215(89)84142-4 contributor: fullname: Barili – volume: 32 start-page: 959 year: 1991 ident: 10.1016/0008-6215(95)00125-D_BIB2_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)92130-0 contributor: fullname: Barili – volume: 33 start-page: 7061 year: 1992 ident: 10.1016/0008-6215(95)00125-D_BIB11 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)60933-4 contributor: fullname: Barili – volume: 100 start-page: 2401 year: 1967 ident: 10.1016/0008-6215(95)00125-D_BIB13 publication-title: Chem. Ber. doi: 10.1002/cber.19671000738 contributor: fullname: Micheel – volume: 46 start-page: 5365 year: 1990 ident: 10.1016/0008-6215(95)00125-D_BIB23 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)87843-1 contributor: fullname: Barili – ident: 10.1016/0008-6215(95)00125-D_BIB18 – start-page: 1625 year: 1987 ident: 10.1016/0008-6215(95)00125-D_BIB20 publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c39870001625 contributor: fullname: Griffith – volume: 17 start-page: 753 year: 1934 ident: 10.1016/0008-6215(95)00125-D_BIB24 publication-title: Helv. Chim. Acta doi: 10.1002/hlca.19340170194 contributor: fullname: Reichstein – start-page: 165 year: 1981 ident: 10.1016/0008-6215(95)00125-D_BIB12 publication-title: Synthesis doi: 10.1055/s-1981-29377 contributor: fullname: Mancuso – volume: 109 start-page: 36888d year: 1988 ident: 10.1016/0008-6215(95)00125-D_BIB9 publication-title: Chem. Abstr. contributor: fullname: Zehner – volume: 124 start-page: 57 year: 1994 ident: 10.1016/0008-6215(95)00125-D_BIB4_2 publication-title: Gazz. Chim. Ital. contributor: fullname: Barili – volume: 122 start-page: 135 year: 1992 ident: 10.1016/0008-6215(95)00125-D_BIB2_2 publication-title: Gazz. Chim. Ital. contributor: fullname: Barili – volume: 48 start-page: 6273 year: 1992 ident: 10.1016/0008-6215(95)00125-D_BIB3 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)88219-3 contributor: fullname: Barili – volume: 71 start-page: 3076 year: 1949 ident: 10.1016/0008-6215(95)00125-D_BIB25 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01177a037 contributor: fullname: Totton – volume: 113 start-page: 3919 year: 1980 ident: 10.1016/0008-6215(95)00125-D_BIB15 publication-title: Chem. Ber. doi: 10.1002/cber.19801131225 contributor: fullname: Köll – volume: 112 start-page: 2296 year: 1979 ident: 10.1016/0008-6215(95)00125-D_BIB16 publication-title: Chem. Ber. doi: 10.1002/cber.19791120636 contributor: fullname: Köll – volume: 212 start-page: c5 year: 1991 ident: 10.1016/0008-6215(95)00125-D_BIB4_1 publication-title: Carbohydr. Res. doi: 10.1016/0008-6215(91)84075-P contributor: fullname: Barili |
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d-galactopyranosides, can be alkylated in their... 3,4-O-Isopropylidene-D-lyxo-hexopyranosid-2-ulose derivatives, obtained by oxidation of 3,4,6-protected D-galactopyranosides, can be alkylated in their anionic... |
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| SubjectTerms | 1,5-Anhydro- d-tagatose 2,5-Dioxabicyclo[2.2.2]octane Acetals - chemical synthesis d-Tagatose Galactose - analogs & derivatives Galactose - chemistry Galactosides - chemistry Hexoses - chemical synthesis Hexoses - chemistry Magnetic Resonance Spectroscopy Molecular Structure Sugar Alcohols - chemistry Sugar Alcohols - standards β- d-Tagatopyranoside |
| Title | New syntheses of d-tagatose and of 1,5-anhydro- d-tagatose from d-galactose derivatives |
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