Caged compounds of a 2-deoxyglucose: Facile synthesis and their photoreactivity

An o-nitrobenzyl and an o-nitrophenethyl derivatized 2-deoxyglucose (caged 2-deoxyglucoses) were synthesized from 3,4,6-tri- O-acetyl-D-glucal in only two steps in moderate to good yields as isomeric mixtures, which were irradiated at 350 nm to afford a 2-deoxyglucose. Decomposition of the o-nitroph...

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Bibliographic Details
Published in:	Bioorganic & medicinal chemistry letters Vol. 8; no. 23; pp. 3375 - 3378
Main Authors:	Watanabe, Soichiro, Hirokawa, Riko, Iwamura, Michiko
Format:	Journal Article
Language:	English
Published:	Oxford Elsevier Ltd 01-12-1998 Elsevier
Subjects:	Chemistry Deoxyglucose - chemical synthesis Deoxyglucose - chemistry Drug Stability Exact sciences and technology General and physical chemistry Magnetic Resonance Spectroscopy Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Nitro compound Aldose Photolysis Glycal Glycoside Photochemical reaction Chemical synthesis
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Summary:	An o-nitrobenzyl and an o-nitrophenethyl derivatized 2-deoxyglucose (caged 2-deoxyglucoses) were synthesized from 3,4,6-tri- O-acetyl-D-glucal in only two steps in moderate to good yields as isomeric mixtures, which were irradiated at 350 nm to afford a 2-deoxyglucose. Decomposition of the o-nitrophenethyl derivative upon photolysis proceeded more efficiently than that of the o-nitrobenzyl derivative. Synthesis and photoreactivity of an o-nitrobenzyl and an o-nitrophenethyl 2-deoxyglucopyranoside will be reported.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0960-894X 1464-3405
DOI:	10.1016/S0960-894X(98)00623-4