ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-α-L-rhamnopyranoside | 148404-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5S,6S)-3-benzoyloxy-2-ethylsulfanyl-5-methoxy-6-methyloxan-4-yl] benzoate
• CAS: 148404-62-0
• 化学式: C₂₃H₂₆O₆S
• 分子量: 430.522
• InChiKey: RXRNTZIPUZJNIU-KVIDMWFFSA-N

物化性质

• 沸点：
  546.4±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Analogues of the mycobacterial arabinogalactan linkage disaccharide as cell wall biosynthesis inhibitors

  摘要：

  The mycobacterial arabinogalactan linkage disaccharide [alpha-(L)-Rha-(1 --> 3)-alpha-D-GlcNAc] provides a basis for the design of new antitubercular drugs, since it supports a key skeletal structure in the bacterial cell wall. A series of analogues of the linker was synthesized by coupling appropriate thiorhamnosyl donors modified at their 4-positions, with an N-acetyl glucosamine acceptor. In a cell-free enzyme inhibition assay, three analogues inhibited the activity of the galactosyltransferase that adds a Galf residue to the linkage disaccharide. Although the compounds were modest inhibitors, these data confirm the viability of this approach to anti-mycobacterial agents. It is especially significant that the three effective compounds are modified at the site of the acceptor atom in the natural substrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00366-3
• 作为产物：
  描述：

  (3aR,4S,6S,7S,7aR)-4-Ethylsulfanyl-7-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 在 吡啶 、 溶剂黄146 作用下， 反应 19.0h， 生成 ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Iodonium ion-assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell-wall glycopeptidolipid of Mycobacterium avium serotype 4

  摘要：

  Condensation of ethyl 2,4-di-O-benzoyl-1-thio-alpha-L-rhamnopyranoside with ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-beta-L-fucopyranoside in the presence of iodonium di-sym-collidine perchlorate afforded exclusively ethyl 2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-1-thio-alpha-L-rhamnopyranoside. This disaccharide derivative was extended at C-1 with 3-benzyloxycarbonylaminopropyl 6-deoxy-3,4-O-isopropylidene-alpha-L-talopyranoside, using N-iodosuccinimide and triflic acid as the catalyst, to furnish 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O[2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-3,4-0-isopropylidene-alpha-L-talopyranoside (20). Selective removal of the chloroacetyl group from 20, followed by condensation with ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-alpha-L-rhamnopyranoside in the presence of the same thiophilic promoter, yielded a fully protected tetrasaccharide derivative. Deprotection of the latter gave the target compound 3-aminopropyl 6-deoxy-2-O-{3-O-[2-O-methyl-(4-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L-fucopyranosyl]-alpha-L-rhamnopyranosyl}alpha-L-talopyranoside (1).

  DOI：

  10.1016/0008-6215(93)80102-k