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ChemInform Abstract: A Chemical Synthesis of 3-Deoxy-D-manno-2-octulosonic Acid from D-Mannose.

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

Publisher
John Wiley and Sons
Year
2009
Weight
34 KB
Volume
40
Category
Article
ISSN
0931-7597

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ChemInform Abstract: A Silicon-Mediated
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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

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