SYNTHESIS OF SOME DEOXY, UNSATURATED, AND DIDEOXY SUGARS VIA REGIOSELECTIVE THIOACYLATION OF GLYCOPYRANOSIDES BY THE DIBUTYLTIN OXIDE METHOD

Treatment of non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, and Me β-D-Xyl) with dibutyltin oxide followed by thioacylation with phenoxythiocarbonyl chloride gave the mono-thiono-carbonates regioselectively in high yields. Acetylation of the latter followed by deoxygenation with...

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Published inChemical & pharmaceutical bulletin Vol. 34; no. 1; pp. 430 - 433
Main Authors Haque, Md. Ekuramul, Kikuchi, Tohoru, Kanemitsu, Kimihiro, Tsuda, Yoshisuke
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1986
Maruzen
Subjects
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
dideoxy sugar
Exact sciences and technology
Organic chemistry
Preparations and properties
Organic thiocarbonate
Glycoside
Regioselectivity
NMR spectrum
Deoxygenation
Acylation
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Summary:Treatment of non-protected glycopyranosides (Me α-D-Glc, Me β-D-Glc, Me α-D-Xyl, and Me β-D-Xyl) with dibutyltin oxide followed by thioacylation with phenoxythiocarbonyl chloride gave the mono-thiono-carbonates regioselectively in high yields. Acetylation of the latter followed by deoxygenation with Bu3SnH smoothly gave the corresponding deoxy derivatives except for the 6-O___--thionocarbonate derivatives. Similar treatment of the pyranosides that have a cis-vicinal glycol (Me α-D-Gal, Me β-D-Gal, Me β-L-Ara, and Ph α-L-Ara) leads to the formation of cyclic thionocarbonates which on acetylation followed by olefination with trimethylphosphite afforded the unsaturated derivatives in satisfactory yields. On deacetylation and subsequent hydrogenation over platinic oxide, they gave the corresponding dideoxy compounds quantitatively.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.34.430