Reaction of Cyclic Thioxocarbonates with Tributyltin Hydride

Treatment of methyl 2-O-acetyl-3, 4-O-thiocarbonyl-β-L-arabinopyranoside with tributyltin hydride produced seven compounds, depending on the reaction conditions : the deoxy derivatives (2 and 3), the methylidene derivative (4), the carbonate (5), the O, S-rearrangement products (7 and 8), and the 4-...

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Published inChemical & pharmaceutical bulletin Vol. 35; no. 9; pp. 3874 - 3879
Main Authors KANEMITSU, KIMIHIRO, TSUDA, YOSHISUKE, HAQUE, MOHAMMED EKRAMUL, TSUBONO, KOJI, TOHRU, KIKUCHI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 25.09.1987
Maruzen
Japan Science and Technology Agency
Subjects
acyl migration
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
cyclic thioxocarbonate
Exact sciences and technology
O, S-rearrangement
Organic chemistry
oxygen trap
Preparations and properties
radical deoxygenation
tributyltin hydride
Gas chromatography
Organic thiocarbonate
Glycoside
Tin Organic compounds
NMR spectrum
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Summary:Treatment of methyl 2-O-acetyl-3, 4-O-thiocarbonyl-β-L-arabinopyranoside with tributyltin hydride produced seven compounds, depending on the reaction conditions : the deoxy derivatives (2 and 3), the methylidene derivative (4), the carbonate (5), the O, S-rearrangement products (7 and 8), and the 4-deoxy acetyl migration product (9). Their structures were determined by spectroscopic and chemical means, and their formation mechanisms are discussed.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.35.3874