Concise synthesis of arabinogalactans with beta-(1 -> 6)-linked galactopyranose backbones and alpha-(1 -> 2)-linked arabinofuranose side chains
文献类型：期刊论文
| 作者 | Li, AX; Kong, FZ |
| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY
 |
| 出版日期 | 2005 |
| 卷号 | 13期号:3页码:839-853 |
| 关键词 | Arabnofuranose Galactopyranose Regio- And Stereo-selective Synthesis |
| DOI | 10.1016/j.bmc.2004.10.035 |
| 英文摘要 | 4-Methoxyphenyl glycosides of 2,3"-bis-alpha-L-arabinofuranosyl branched beta-D-(1-6)-linked galactopyranosyl tetraose (16), 3',2""-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked Plactopyranosyl hexaose (27), and a twentyose (42) consisting of beta- (1-->6)-linked D-galactopyranosyl pen tadecaoligosaccha ride backbone with alpha-L-arabinofuranosyl side chains alternatively attached at C-2 and C-3 of the middle galactose residue of each consecutive beta-(1-->6)-linked galactotriose unit of the backbone. were synthesized with isopropyl 3-O-allyl-2.4-di-O-benzoyl-1-thio-beta-D-galactopyranoside (6). 2.3.4.6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (7), 2,.3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl trichloroacetimidate (12), 6-O-acetyl-2,3,4-tn-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (17), 4-methoxyphenyl 2,3,4-tri-O-benzo-beta-D-galactopyranoside (19), and 2,6-di-O-acetyl-3,4-di-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate (28) as the key synthons. Condensation of 6 with 7 gave the disaccharide donor 8, and subsequent condensation of 8 with 4-methoxyphenyl 2.3.4-tri-O-benzoyl-beta-D-galactopyranosyl-(1-->6)-2-O-acetyl-3,4-di-O-benzoyl-beta-D-galactopyranoside (9) followed by selective deacetylation afforded the tetrasaccharide acceptor 11. Coupling of I I with 12 gave the pentasaccharide 13, its deallylation followed by coupling with 12. and debenzoylation Rave the hexasaccharide 16 with beta-(1-->6)-linked galactopyranose backbone and 2- and 3"-linked alpha-L-arabinofuranose side chains. The octasaccharide 27 was similarly synthesized, while the twentyoside 42 was synthesized with tetrasaccharides 33 or 24 as the donors and 23, 36, 38, and 40 as the acceptors by consecutive couplings followed by deacylation. (C) 2004 Elsevier Ltd. All rights reserved. |
| 学科主题 | Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry |
| WOS研究方向 | Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry |
| WOS记录号 | WOS:000226676800025 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/23366]  |
| 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 | Li, AX,Kong, FZ. Concise synthesis of arabinogalactans with beta-(1 -> 6)-linked galactopyranose backbones and alpha-(1 -> 2)-linked arabinofuranose side chains[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2005,13(3):839-853. |
| APA | Li, AX,&Kong, FZ.(2005).Concise synthesis of arabinogalactans with beta-(1 -> 6)-linked galactopyranose backbones and alpha-(1 -> 2)-linked arabinofuranose side chains.BIOORGANIC & MEDICINAL CHEMISTRY,13(3),839-853. |
| MLA | Li, AX,et al."Concise synthesis of arabinogalactans with beta-(1 -> 6)-linked galactopyranose backbones and alpha-(1 -> 2)-linked arabinofuranose side chains".BIOORGANIC & MEDICINAL CHEMISTRY 13.3(2005):839-853. |
入库方式： OAI收割
来源：生态环境研究中心
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