Amadori ketoses with calcium hydroxide and the Kiliani reaction on 1-deoxy ketoses: two approaches to the synthesis of saccharinic acids
Amadori ketoses with calcium hydroxide and the Kiliani reaction on 1-deoxy ketoses: two approaches to the synthesis of saccharinic acids
复制标题
DOI：
10.1016/j.tetlet.2005.11.018
复制
发表时间：
2006-01-16
影响因子：
1.8
通讯作者：
Fleet, GWJ
中科院分区：
文献类型：
--
作者：
Hotchkiss, DJ;Jenkinson, SF;Fleet, GWJ
糖精酸（2-C-甲基醛糖酸）可以通过用氢氧化钙处理Amadori酮糖或通过1-脱氧酮糖与氰化物的Kiliani反应来形成。因此，(i)N，N-二苄基或N，N-二甲基-1-氨基-1-脱氧-D-果糖与氢氧化钙水溶液在绿色条件下得到2-C-甲基-D-核糖-1，4-内酯，并且(ii)甲基溴化镁与2，3-O-异亚丙基-D-赤藓糖内酯反应得到 1-脱氧-3,4-O-异亚丙基-D-核酮糖，随后用氰化钠水溶液处理并水解，形成2-C-甲基-D-阿拉伯酮-1,4-内酯。这种支链糖内酯可能作为含有支链碳链的凯龙具有价值。 (c) 2005 年，爱思唯尔有限公司出版。
Saccharinic acids (2-C-methyl aldonic acids) may be formed by treatment of Amadori ketoses with calcium hydroxide or by the Kiliani reaction of 1-deoxy ketoses with cyanide. Thus (i) N,N-dibenzyl or N,N-dimethyl-1-amino-1-deoxy-D-fructose with aqueous calcium hydroxide afforded 2-C-methyl-D-ribono-1,4-lactone under green conditions and (ii) reaction of methyl magnesium bromide with 2,3-O-isopropylidene-D-erythronolactone gave 1-deoxy-3,4-O-isopropylidene-D-ribulose, which on subsequent treatment with aqueous sodium cyanide and hydrolysis, formed 2-C-methyl-D-arabinono-1,4-lactone. Such branched sugar lactones are likely to be of value as chirons containing branched carbon chains. (c) 2005 Published by Elsevier Ltd.