Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

被引：6

作者：

Burugupalli, Satvika

Shah, Sayali

van der Peet, Phillip L.

Arora, Seep

White, Jonathan M.

Williams, Spencer J. ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 01期

基金：

澳大利亚研究理事会;

关键词：

REGIOSELECTIVE ACYLATION; PEPTIDE-SYNTHESIS; DERIVATIVES; EFFICIENT; ESTERS; DIOLS; 1-HYDROXYBENZOTRIAZOLE; CYCLIZATION; CONVENIENT; GLUCOSE;

D O I：

10.1039/c5ob02092a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroxybenzotriazole (HOBt) and HOBt-derived reagents have been classified as Class I explosives, with restrictions on their transportation and storage. We explored a range of benzoylated oxime-based reagents as alternatives to benzoyloxybenzotriazole (BBTZ) for the selective benzoylation of carbohydrate polyols. Benzoylated oximes derived from 2-hydroximino-malononitrile, ethyl 2-hydroximino-2-cyanoacetate (Oxyma), and tert-butyl 2-hydroximino-2-cyanoacetate were most effective for benzoylation of a simple primary alcohol, with yields approaching that obtained for BBTZ. When applied to carbohydrate diols, the most effective reagent was identified as benzoyl-Oxyma. Benzoyl-Oxyma is a highly crystalline, readily prepared alternative to BBTZ, useful in the selective benzoylation of carbohydrate polyols.

引用

页码：97 / 104

页数：8

共 46 条

[11] An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: a mechanistic perception [J].