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A Silicon-Mediated Synthesis of 3-Deoxy-D-manno-octulosonic Acid (KDO)

✍ Scribed by Nico Bräuer; Andreas Kirschning; Ernst Schaumann

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
115 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

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 deprotection procedures. silyl dithioacetal 7, followed by acylation of the alcoholate,

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ChemInform Abstract: A Silicon-Mediated
ChemInform Abstract: A Silicon-Mediated Synthesis of 3-Deoxy-D-manno-octulosonic Acid (KDO).
✍ Nico Braeuer; Andreas Kirschning; Ernst Schaumann 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

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