Selective and facile deacetylation of pentacyclic triterpenoid under methanolic ammonia condition and unambiguous NMR analysis

doi:10.1016/j.cclet.2019.06.007

	Selective and facile deacetylation of pentacyclic triterpenoid under methanolic ammonia condition and unambiguous NMR analysis
	Wang, Han 1,3; Xu, Renyang 1; Liang, Shuobin 1; Ran, Fuxiang 1; Zhang, Lihe 1; Zhang, Yongmin 4; Zhou, Demin 1; Xiao, Sulong 1,2
通讯作者	Xiao, Sulong(slxiao@bjmu.edu.cn)
	2020-02-01
发表期刊	CHINESE CHEMICAL LETTERS
ISSN	1001-8417
卷号	31 期号:2 页码:333-336
摘要	The acetyl ester plays an important role for protection of the hydroxyl groups in carbohydrates synthesis. In the present study, we described an efficient deprotection of acetyl group of pentacyclic triterpenoid by using methanolic ammonia in THE solution. Good selectivity for cleaving gal-C2-OAc group of 3 beta-hydroxy-olean-12-en-28-oic acid 28-N-2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside (3) was achieved in the presence of methanolic ammonia within 4 h at low temperature (-60 degrees C) in a yield of 56%. The reaction disclosed here provides a new method for the synthesis of C2 selective modified carbohydrates, which is more useful than conventional synthesis procedure that usually requires many steps including temporary regioselective protection and deprotection. When the reaction temperature was increased from -60 degrees C to room temperature, the cleavage of the other three acetyl groups of galactose in an order of C4-OAc > C3-OAc > C6-OAc was observed. Based on this study, a plausible route for the deacetylation reaction has been proposed. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
关键词	Pentacyclic triterpenoid Deacetylation Methanolic ammonia Selectivity Synthesis
DOI	10.1016/j.cclet.2019.06.007
收录类别	SCI ; SCI
语种	英语
WOS记录号	WOS:000510956700005
引用统计	被引频次：1[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/70865
专题	植物化学与西部植物资源持续利用国家重点实验室
通讯作者	Xiao, Sulong
作者单位	1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 3.Dalian Med Univ, Affiliated Hosp 2, Dept Pharm, Dalian 116023, Peoples R China 4.Sorbonne Univ, Inst Parisien Chim Mol, CNRS UMR 8232, 4 Pl Jussieu, F-75005 Paris, France
推荐引用方式 GB/T 7714	Wang, Han,Xu, Renyang,Liang, Shuobin,et al. Selective and facile deacetylation of pentacyclic triterpenoid under methanolic ammonia condition and unambiguous NMR analysis[J]. CHINESE CHEMICAL LETTERS,2020,31(2):333-336.
APA	Wang, Han.,Xu, Renyang.,Liang, Shuobin.,Ran, Fuxiang.,Zhang, Lihe.,...&Xiao, Sulong.(2020).Selective and facile deacetylation of pentacyclic triterpenoid under methanolic ammonia condition and unambiguous NMR analysis.CHINESE CHEMICAL LETTERS,31(2),333-336.
MLA	Wang, Han,et al."Selective and facile deacetylation of pentacyclic triterpenoid under methanolic ammonia condition and unambiguous NMR analysis".CHINESE CHEMICAL LETTERS 31.2(2020):333-336.