Synthesis of 3-deoxy-6-thio-d-manno-2-octulosonic acid (“6-thio-KDO”)
✍ Scribed by Björn Classon; Per J. Garegg; Zhengchun Liu; Bertil Samuelsson
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- English
- Weight
- 419 KB
- Volume
- 174
- Category
- Article
- ISSN
- 0008-6215
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
## 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
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
The 8-C-lithiated acrylamide 3A has been proven to be an ideal pyruvate 8-carbanion equivalent useful in a highly diastereoselective KDO synthesis. The starting material 3 was prepared from pyruvate diethyl acetal in four convenient steps. Direct lithiation with 2 equiv. of LDA generated the dilithi