Synthesis of C-glycosyl amino acids:: scope and limitations of the tandem Tebbe/Claisen approach
Synthesis of C-glycosyl amino acids:: scope and limitations of the tandem Tebbe/Claisen approach
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DOI：
10.1016/j.tetasy.2004.11.035
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发表时间：
2005-01-10
影响因子：
--
通讯作者：
Fairbanks, AJ
中科院分区：
文献类型：
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作者：
Chambers, DJ;Evans, GR;Fairbanks, AJ
Amino acids may be used as coupling partners for esterification with 3-hydroxy galycals as substrates for the tandem Tebbe/Claisen approach to the synthesis of C-glycosyl amino acids. Whilst esters of substituted at-amino acids do not successfully undergo Tebbe, or other, methylenation, esters of beta- or gamma-amino acids are methylenated to yield vinyl ethers. which then undergo smooth thermal rearrangement to yield beta-C-glycoside products. tert-Butyl esters are found to be unreactive to the Tebbe reagent, and as such tert-butyl protection may be used for other carboxylic acids. (C) 2004 Elsevier Ltd. All rights reserved.
