用于捕获碳水化合物和核苷磷酸化的固相试剂。

A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides.

作者信息

Parang K, Fournier E J, Hindsgaul O

机构信息

Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada.

出版信息

Org Lett. 2001 Jan 25;3(2):307-9. doi: 10.1021/ol0069498.

DOI:10.1021/ol0069498

PMID:11430061

Abstract

[figure: see text] A 1% cross-linked divinylbenzene-polystyrene copolymer, containing cyanoethoxy N,N-diisopropylamine phosphine was prepared as a phosphitylating agent. The polymer-bound phosphitylated precursor was subjected to reaction with alcohols in the presence of 1H-tetrazole to produce the corresponding polymer-bound phosphite triesters. These were then oxidized with tert-butyl hydroperoxide to give the polymer-bound monophosphate triesters. Removal of cyanoethoxy on the resin with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by basic cleavage of the p-hydroxybenzyl linker products yielded monophosphate derivatives.

摘要

[图：见正文] 制备了一种含氰乙氧基N，N-二异丙胺膦的1%交联二乙烯基苯-聚苯乙烯共聚物作为磷酰化剂。使聚合物键合的磷酰化前体在1H-四唑存在下与醇反应，生成相应的聚合物键合亚磷酸三酯。然后用叔丁基过氧化氢将这些亚磷酸三酯氧化，得到聚合物键合的单磷酸三酯。用1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）除去树脂上的氰乙氧基，随后对对羟基苄基连接产物进行碱性裂解，得到单磷酸衍生物。