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Synthesis of a 3-deoxy-d-manno-octulosonic acid (KDO) building block from d-glucose via fermentation

✍ Scribed by Camci-Unal, Gulden; Mizanur, Rahman M.; Chai, Yonghai; Pohl, Nicola L. B.


Book ID
118165269
Publisher
Royal Society of Chemistry
Year
2012
Tongue
English
Weight
642 KB
Volume
10
Category
Article
ISSN
1477-0520

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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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A Silicon-Mediated Synthesis of 3-Deoxy-D-manno-octulosonic Acid (KDO). -Starting from commercially available D-mannitol (I), the synthesis of KDO ammonium salt (VII) includes, as key steps, a silicon-mediated epoxide ring opening reaction of (II) and silicon-induced lactonization of carbonate (V) w