Syntheses of higher sugars by a new chain-elongation reaction

The reaction of methyl 2,3,4-tri- O-acetyl-6-deoxy-6-nitro-α- d-glucopyranoside and 3,4,5,7-tetra- O-acetyl-2,6-anhydro-1-deoxy-1-nitro- d- glycero- l- manno-heptitol with carbon disulfide, methyl iodide, and sodium hydride gave methyl 2,3,4-di- O-acetyl-6,7-dideoxy-7,7-bis(methylthio)-6-nitro-α- d-...

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Bibliographic Details
Published in:Carbohydrate research 1989-12, Vol.194, p.87-93
Main Authors: Peseke, Klaus, Ambrosi, Horst-Dieter, Michalik, Manfred
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:The reaction of methyl 2,3,4-tri- O-acetyl-6-deoxy-6-nitro-α- d-glucopyranoside and 3,4,5,7-tetra- O-acetyl-2,6-anhydro-1-deoxy-1-nitro- d- glycero- l- manno-heptitol with carbon disulfide, methyl iodide, and sodium hydride gave methyl 2,3,4-di- O-acetyl-6,7-dideoxy-7,7-bis(methylthio)-6-nitro-α- d- gluco-hept-6-enopyranoside ( 3) and 4,5,6,8-tetra- O-acetyl-3,7-anhydro-2-deoxy-2-nitro- d- glycero- l- manno-oct-1-enose dimethyl dithioacetal, respectively. Substitution reactions of 3 were investigated.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(89)85009-8