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- W1981911474 abstract "Stereocontrolled, stepwise synthesis of decyl glycosides of alpha-(1-->2)-linked di- to pentaglucosides (1-5) is described; these constitute fragments of Polysaccharide II of Mycobacterium tuberculosis. Phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha-D- glucopyranoside (7) was used as the single key intermediate, obtained from 1,3,4,6-tetra-O-acetyl-2-O-benzyl-beta-D-glucopyranose (6) and PhSSiMe3. Halogenolysis of 7 afforded the isolated beta bromide (10) and beta chloride (13). Solvolysis of 10 with decanol without heavy metal salts gave decyl 3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranoside (14) in a highly stereoselective reaction, in high yield. Subsequent, iterative hydrogenolytic removal of the O-benzyl group and glycosylation with the beta-chloride 13 under catalysis by silver salts afforded the protected di- to penta-saccharide glycosides 16, 19, 21, and 23, which were conventionally deblocked." @default.
- W1981911474 created "2016-06-24" @default.
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- W1981911474 date "1995-11-01" @default.
- W1981911474 modified "2023-09-26" @default.
- W1981911474 title "Synthesis of a pentasaccharide fragment of Polysaccharide II of Mycobacterium tuberculosis" @default.
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- W1981911474 doi "https://doi.org/10.1016/0008-6215(95)00199-4" @default.
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