A highly convergent and effective synthesis of the phytoalexin elicitor hexasaccharide
文献类型：期刊论文
| 作者 | Wang, W; Kong, FZ |
| 刊名 | CARBOHYDRATE RESEARCH
 |
| 出版日期 | 1999 |
| 卷号 | 315期号:2015-01-02页码:117-127 |
| 关键词 | Synthesis Elicitor-active D-glucohexatose Orthoester Rearrangement |
| DOI | 10.1016/S0008-6215(99)00003-8 |
| 英文摘要 | The peracetylated hexasaccharide 1,2,4-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-6-O-(2,4-di-O-acetyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranosyl)-beta-D-glucopyranosyl)-alpha,beta-D-glucopyranose 21 was synthesized in a blockwise manner, employing trisaccharide trichloroacetimidate 2,4-di-O-acetyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoyl)-alpha-D-glucopyranosyl trichloroacetimidate 17 as the glycosyl donor, and trisaccharide 4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-beta-D-glucopyranosyl)-1,2-O-(R,S)ethylidene-alpha-D-glucopyranose 18 as the acceptor. The donor 17 and acceptor 18 were readily prepared from trisaccharides 3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-beta-D-glucopyranosyl)-1,2-O -(R,S)ethylidene-alpha-D-glucopyranose 10 and 3,6-di-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2-O-(R,S)ethylidene-alpha-D-glucopyranose 11, respectively, which were obtained from rearrangement of orthoesters 3,4-di-O-acetyl-6-O-chloroacetyl-alpha-D-glucopyranose 1,2-(3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2-O-(R,S)ethylidene-alpha-D-glucopyranosid-6-yl orthoacetate) 8 and 3,4,6-tri-O-acetyl-alpha-D-glucopyranose 1,2-(3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2-O-(R, S)ethylidene-alpha-D-glucopyranosid-6-yl orthoacetate) 9, respectively. The orthoesters were prepared from selective coupling of the disaccharide 3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)- 1,2-O-(R,S)ethylidene-alpha-D-glucopyranose 4 with 'acetobromoglucose' (tetra-O-acetyl-alpha-D-glucopyranosyl bromide) and 6-O-chloroacetylated 'acetobromoglucose', respectively. To confirm the selectivity of the orthoester formation and rearrangement, the disaccharide 4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2-O-(R,S)ethylidene-alpha-D-glucopyranose 7 was prepared from 4 by selective tritylation, acetylation and detritylation. The title compound, an elicitor-active D-glucohexaose 3-O-(beta-D-glucopyranosyl)6-O-(6-O-(3,6-di-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl)-beta-D-glucopyranosyl)-alpha,beta-D-glucopyranose 1, was finally obtained by Zemplen deacetylation of 21 in quantitative yield. (C) 1999 Elsevier Science Ltd. All rights reserved. |
| WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
| WOS记录号 | WOS:000080700200011 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/24240]  |
| 专题 | 生态环境研究中心_中国科学院环境生物技术重点实验室 |
| 推荐引用方式 GB/T 7714 | Wang, W,Kong, FZ. A highly convergent and effective synthesis of the phytoalexin elicitor hexasaccharide[J]. CARBOHYDRATE RESEARCH,1999,315(2015-01-02):117-127. |
| APA | Wang, W,&Kong, FZ.(1999).A highly convergent and effective synthesis of the phytoalexin elicitor hexasaccharide.CARBOHYDRATE RESEARCH,315(2015-01-02),117-127. |
| MLA | Wang, W,et al."A highly convergent and effective synthesis of the phytoalexin elicitor hexasaccharide".CARBOHYDRATE RESEARCH 315.2015-01-02(1999):117-127. |
入库方式： OAI收割
来源：生态环境研究中心
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