Reaction of Cyclic Thioxocarbonates with Tributyltin Hydride

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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Veröffentlicht in:Chemical & pharmaceutical bulletin 1987/09/25, Vol.35(9), pp.3874-3879
Hauptverfasser: KANEMITSU, KIMIHIRO, TSUDA, YOSHISUKE, HAQUE, MOHAMMED EKRAMUL, TSUBONO, KOJI, TOHRU, KIKUCHI
Format: Artikel
Sprache:eng
Schlagworte:
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
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Beschreibung
Zusammenfassung: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