ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside | 877606-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside
• CAS: 877606-75-2
• 化学式: C₃₇H₄₆O₁₀S
• 分子量: 682.832
• InChiKey: LZGATJXTBYLNLM-FBHNISPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  122.14
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannnopyranosyl-(1->2)-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)]-3-O-acetyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the pentasaccharide repeating unit of latosillan

  摘要：

  A pentasaccharide, beta-D-Man-(1 -> 2)-[beta-D-GlcNAc-(1 -> 4)]-alpha-L-Rha-(1 -> 4)-alpha-L-Rha-(1 -> 4)-alpha-L-Rha-1-OC8H17, representing the repeating unit of latosillan, was convergently synthesized from the building blocks, ethyl 2,3-O-isopropylidene-1-thio-alpha-L-rhamnopyranoside, 2-O-acetyl-3,4,6-tri-O-belizyl-beta-D-glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2phthalimido-beta-D-glueopyranosyl trichloroacetimidate under standard glycosylation conditions. The target pentasaccharide showed acceptable differentiation-inducing activity on HL-60 cell lines at the dosages of 10-50 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.11.007
• 作为产物：
  描述：

  ethyl 1-thio-α-L-rhamnopyranoside 在 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 对甲苯磺酸 、 二甲基亚砜 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 23.5h， 生成 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the pentasaccharide repeating unit of latosillan

  摘要：

  A pentasaccharide, beta-D-Man-(1 -> 2)-[beta-D-GlcNAc-(1 -> 4)]-alpha-L-Rha-(1 -> 4)-alpha-L-Rha-(1 -> 4)-alpha-L-Rha-1-OC8H17, representing the repeating unit of latosillan, was convergently synthesized from the building blocks, ethyl 2,3-O-isopropylidene-1-thio-alpha-L-rhamnopyranoside, 2-O-acetyl-3,4,6-tri-O-belizyl-beta-D-glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2phthalimido-beta-D-glueopyranosyl trichloroacetimidate under standard glycosylation conditions. The target pentasaccharide showed acceptable differentiation-inducing activity on HL-60 cell lines at the dosages of 10-50 mu g/mL. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.11.007