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Studies of the synthesis of sugar phosphonates related to 3-deoxy-d-manno-2-octulosonic acid (Kdo)

✍ Scribed by H»kan Molin; Jan-Olof Norèn; Alf Claesson

Publisher
Elsevier Science
Year
1989
Tongue
English
Weight
863 KB
Volume
194
Category
Article
ISSN
0008-6215

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Synthesis of 3-deoxy-D-manno-2-octuloson
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## Abstract [(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide (8), obtained from glyoxylic acid via a convenient one‐pot procedure, reacted in a Wittig reaction with 4‐__O__‐benzyl‐2,3:5,6‐di‐__O__‐isopropylidene‐D‐mannose (7), readily synthesized on a large scale from D‐mannose, t

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KDO (1) is synthesized in five steps, starting from 1,2-to the carbonate 9. Silicon-induced lactonization affords the lactone 10, which can be converted into NH 4 -KDO by anhydro-3,4:5,6-di-O-isopropylidene-D-mannitol ( 6). The epoxide 6, obtained from D-mannitol (2), reacts with lithiated standard

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Glycosylation of methyl (ally1 7,8-0-carbonyl-3-deoxy-a-D-manno-2-octulopyranosid)onate with an (w-(2+4) linked per-0-acetylated KDO-disaccharide bromide derivative under Helferich conditions afforded a 2: 1 mixture of the (Y-and p-linked trisaccharide derivatives in 50% yield. Removal of the protec