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Total Synthesis of 3-Deoxy- d - manno -2-octulosonic Acid (KDO) and 2-Deoxy-β-KDO

✍ Scribed by Burke, Steven D.; Sametz, Geoffrey M.

Book ID
121321478
Publisher
American Chemical Society
Year
1999
Tongue
English
Weight
65 KB
Volume
1
Category
Article
ISSN
1523-7060

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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

A Silicon-Mediated Synthesis of 3-Deoxy-
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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