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

文献类型：期刊论文

作者Wang, Han3,4; Xu, Renyang4; Liang, Shuobin4; Ran, Fuxiang4; Zhang, Lihe4; Zhang, Yongmin1; Zhou, Demin4; Xiao, Sulong2,4
刊名CHINESE CHEMICAL LETTERS
出版日期2020-02-01
卷号31期号:2页码:333-336
关键词Pentacyclic triterpenoid Deacetylation Methanolic ammonia Selectivity Synthesis
ISSN号1001-8417
DOI10.1016/j.cclet.2019.06.007
通讯作者Xiao, Sulong(slxiao@bjmu.edu.cn)
英文摘要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.
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000510956700005
源URL[http://ir.kib.ac.cn/handle/151853/70864]  
专题昆明植物研究所_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.Sorbonne Univ, Inst Parisien Chim Mol, CNRS UMR 8232, 4 Pl Jussieu, F-75005 Paris, France
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.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
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.

入库方式： OAI收割

来源：昆明植物研究所

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