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A Chemical Synthesis of 3-Deoxy-D- manno -2-octulosonic Acid from D-mannose

✍ Scribed by Ichiyanagi, Tsuyoshi; Sakamoto, Naoko; Ochi, Kazutoshi; Yamasaki, Ryohei


Book ID
121237570
Publisher
Taylor and Francis Group
Year
2009
Tongue
English
Weight
525 KB
Volume
28
Category
Article
ISSN
0732-8303

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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