Methyl 2-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside | 137439-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-4,5-dibenzoyloxy-6-[(2R,3R,4R,5S,6S)-5-hydroxy-2-methoxy-6-methyl-3-[(2R,3S,4R,5R,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyoxan-4-yl]oxy-2-methyloxan-3-yl] benzoate
• CAS: 137439-15-7
• 化学式: C₆₁H₅₈O₁₉
• 分子量: 1095.12
• InChiKey: WHEOIRQVONGDPJ-ITKYRHGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  80.0
• 可旋转键数：
  17.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  233.41
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Methyl 2-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以95%的产率得到Methyl 2-O-(β-L-fucopyranosyl)-3-O-(β-L-rhamnopyranosyl)-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
• 作为产物：
  描述：

  methyl 4-O-benzyl-3-O-(4-methoxybenzyl)-α-L-rhamnopyranoside 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 氢气 、 氰化汞 、 1,1,3,3-四甲基脲 、 mercury dibromide 作用下， 以 硝基甲烷 、 乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.16h， 生成 Methyl 2-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-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