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ChemInform Abstract: A Silicon-Mediated Synthesis of 3-Deoxy-D-manno-octulosonic Acid (KDO).

✍ Scribed by Nico Braeuer; Andreas Kirschning; Ernst Schaumann


Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


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) with Bu 4


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A Silicon-Mediated Synthesis of 3-Deoxy-
✍ Nico BrΓ€uer; Andreas Kirschning; Ernst Schaumann πŸ“‚ Article πŸ“… 1998 πŸ› John Wiley and Sons 🌐 English βš– 115 KB πŸ‘ 2 views

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