Methyl 2-O-acetyl-4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside | 137438-95-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2-O-acetyl-4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-[(2R,3R,4R,5S,6S)-3-acetyloxy-5-benzoyloxy-2-methoxy-6-methyloxan-4-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 137438-95-0
• 化学式: C₅₀H₄₆O₁₆
• 分子量: 902.906
• InChiKey: VPGBBHLIOUKNMJ-MRLWUMFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  66.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Methyl 2-O-acetyl-4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 在 盐酸 、 4 A molecular sieve 、 nitrosonium tetrafluoroborate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 18.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4R,5S,6S)-5-benzoyloxy-2-methoxy-6-methyl-3-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-4-yl]oxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Synthesis of di-O-glycosyl derivatives of methyl α-l-rhamnopyranoside

  摘要：

  The syntheses are described of 2,3-di-O-glycosyl derivatives (1-12) of methyl alpha-L-rhamnopyranoside where the glycosyl moieties are variously alpha-L-fucopyranose, beta-L-fucopyranose, beta-D-glucopyranose, alpha-D-mannopyranose, and alpha-L-rhamnopyranose. The syntheses involve stereoselective glycosylation of methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-alpha-L-rhamnopyranoside (21), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)-alpha-L-rhamnopyranoside (25), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside (29), methyl 4-O-benzoyl-3-O-(2, 3,4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L-rhamnopyranoside (35), and methyl 4-O-benzyl-2-O-(2,3, 4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L-rhamnopyranoside (59). In the syntheses of compounds 7-9, the alpha-L-fucopyranosyl residues are introduced stereoselectively, using 2,3,4-tri-O-benzoyl-alpha-L-fucopyranosyl bromide (17) and ethyl 2,3,4-tri-O-acetyl-l-thio-beta-L-fucopyranoside (47) as glycosyl donors.

  DOI：

  10.1016/0008-6215(92)80010-x
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6S)-6-[(2R,3R,4R,5S,6S)-3-acetyloxy-2-methoxy-6-methyl-5-phenylmethoxyoxan-4-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate 在 palladium on activated charcoal 吡啶 、 4-dimethylpyridine 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 37.0~40.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 Methyl 2-O-acetyl-4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of di-O-glycosyl derivatives of methyl α-l-rhamnopyranoside

  摘要：

  The syntheses are described of 2,3-di-O-glycosyl derivatives (1-12) of methyl alpha-L-rhamnopyranoside where the glycosyl moieties are variously alpha-L-fucopyranose, beta-L-fucopyranose, beta-D-glucopyranose, alpha-D-mannopyranose, and alpha-L-rhamnopyranose. The syntheses involve stereoselective glycosylation of methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-alpha-L-rhamnopyranoside (21), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)-alpha-L-rhamnopyranoside (25), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside (29), methyl 4-O-benzoyl-3-O-(2, 3,4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L-rhamnopyranoside (35), and methyl 4-O-benzyl-2-O-(2,3, 4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L-rhamnopyranoside (59). In the syntheses of compounds 7-9, the alpha-L-fucopyranosyl residues are introduced stereoselectively, using 2,3,4-tri-O-benzoyl-alpha-L-fucopyranosyl bromide (17) and ethyl 2,3,4-tri-O-acetyl-l-thio-beta-L-fucopyranoside (47) as glycosyl donors.

  DOI：

  10.1016/0008-6215(92)80010-x