𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Alkylidenecarbene insertion at anomeric CH bonds. Synthesis of 3-deoxy-d-arabino-2-heptulosonic acid (DAH) and 3-deoxy-d-manno-2-octulosonic acid (KDO)

✍ Scribed by Duncan J Wardrop; Wenming Zhang

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
96 KB
Volume
43
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

A novel method for the homologation of glycals to the corresponding 3-deoxy-2-ulosonic acids, based on the [1,5]-C H bond insertion of alkylidenecarbenes, is presented. The application of this approach is illustrated through the synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO).

📜 SIMILAR VOLUMES

Synthesis of 3-deoxy-D-manno-2-octuloson
Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO)
✍ Frick, Wendelin ;Krülle, Thomas ;Schmidt, Richard R. 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 423 KB

## 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

Vinyl Carbanions. Part 36.. Synthesis of
Vinyl Carbanions. Part 36.. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and derivatives
✍ Angelika Esswein; Rainer Betz; Richard R. Schmidt 📂 Article 📅 1989 🏛 John Wiley and Sons 🌐 German ⚖ 728 KB

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