Methyl 2-O-acetyl-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-α-L-rhamnopyranoside | 135129-71-4

• 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-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-6-[(2R,3R,4R,5S,6S)-3-acetyloxy-5-hydroxy-2-methoxy-6-methyloxan-4-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate
• CAS: 135129-71-4
• 化学式: C₃₆H₃₈O₁₃
• 分子量: 678.69
• InChiKey: RFPSYXWNZOOGHO-OKEVHDPZSA-N

物化性质

• 沸点：
  767.2±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  162.35
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Methyl 2-O-acetyl-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-α-L-rhamnopyranoside 在 吡啶 、 盐酸 、 4-dimethylpyridine 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 34.0h， 生成 Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-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 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-α-L-rhamnopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 以94%的产率得到Methyl 2-O-acetyl-3-O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-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

文献信息

• Khatuntseva; Shashkov; Nifant'ev, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 5, p. 325 - 331
  作者：Khatuntseva、Shashkov、Nifant'ev

  DOI：——

  日期：——
• NIFANTEV, N. EH.;BAKINOVSKIJ, L. V.;LIPKIND, G. M.;SHASHKOV, A. S.;KOCHET+, BIOORGAN. XIMIYA, 17,(1991) N, S. 517-530
  作者：NIFANTEV, N. EH.、BAKINOVSKIJ, L. V.、LIPKIND, G. M.、SHASHKOV, A. S.、KOCHET+

  DOI：——

  日期：——