Synthesis of a 3-deoxy-d-manno-octulosonic acid (KDO) building block from d-glucose via fermentation
β 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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π SIMILAR VOLUMES
## Abstract [(Benzyloxy)(benzyloxycarbonyl)methyl]triphenylphosphonium bromide (8), obtained from glyoxylic acid via a convenient oneβpot procedure, reacted in a Wittig reaction with 4β__O__βbenzylβ2,3:5,6βdiβ__O__βisopropylideneβDβmannose (7), readily synthesized on a large scale from Dβmannose, t
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
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