methyl 2,4-di-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside | 89202-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-5-benzoyloxy-6-methoxy-2-methyl-4-phenylmethoxyoxan-3-yl] benzoate
• CAS: 89202-43-7
• 化学式: C₂₈H₂₈O₇
• 分子量: 476.526
• InChiKey: GJKOAQWUCYQBGL-GAQITVIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,4-di-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以574.5 mg的产率得到methyl 4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  用于催化糖基化的正戊烯基型糖苷及其在单催化剂单罐寡糖装配中的应用。

  摘要：

  我们已经开发出一种新型的正戊烯基型糖苷，可以在室温下通过催化量的启动子Hg（NTf 2）2或PPh 3 AuCl / AgNTf 2进行活化。普通保护/去保护操作的温和活化条件和出色的稳定性使烯丙基供体在构建各种糖苷键方面具有广泛的应用。此外，在Hg（NTf 2）2催化的条件下，实现了不同类型供体的顺序活化，在此基础上，通过新开发的单催化剂一锅法合成了龙胆四糖。

  DOI：

  10.1021/acs.orglett.9b03038
• 作为产物：
  描述：

  苯甲醇 在 三氟甲磺酸 sodium hydride 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 19.58h， 生成 methyl 2,4-di-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Wessel, Hans-Peter; Iversen, Tommy; Bundle, David R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2247 - 2250

  摘要：

  DOI：

文献信息

• Pozsgay, Vince, Journal of the American Chemical Society, 1995, vol. 117, # 25, p. 6673 - 6681
  作者：Pozsgay, Vince

  DOI：——

  日期：——
• Synthesis of ligands related to the O-specific antigen of type 1 Shigella dysenteriae. 3. Glycosylation of 4,6-O-substituted derivatives of methyl 2-acetamido-2-deoxy-.alpha.-D-glucopyranoside with glycosyl donors derived from mono- and oligosaccharides.
  作者：Pavol Kovac、Kevin J. Edgar

  DOI：10.1021/jo00034a047

  日期：1992.4

  Methyl O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside, obtained by silver trifluoromethanesulfonate-mediated condensation of methyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside and 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl bromide (3), was cleaved with dichloromethyl methyl ether (DCMME) to give O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl chloride (9). Condensations of 1,3,4,6-tetra-O-acetyl-alpha-D-galactopyranose with 3 and 9, followed by treatment of the products with DCMME yielded, respectively, glycosyl chlorides 12 and 17. Each of these, as well as 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride was condensed with 4,6-O-substituted (benzylidene, tetraisopropyl-disiloxane-1,3-diyl, or benzyl) derivatives of methyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside, using CH2Cl2, ether, or a mixture thereof as the solvent. The formation of the desired alpha-D-galactopyranosyl linkage was favored when ether was the solvent. Under these conditions, however, the combined yield of the condensation products decreased, especially when less reactive synthons were used. The alpha-linked products obtained were deprotected to give the methyl alpha-glycosides of the tetra, tri-, and the disaccharide related to the chemical repeating unit of the O-specific side chain of the lipopolysaccharide of Shigella dysenteriae type 1. Synthesis of methyl alpha-glycosides of three other constituents of the same polymeric antigen [alpha-L-Rha-(1 --> 3)-alpha-L-Rha, alpha-L-Rha-(1 --> 2)-alpha-D-Gal, and alpha-L-Rha-(1 --> 3)-alpha-L-Rha-(1 --> 2)-alpha-D-Gal] are also described.