ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-O-(2',3'-diethoxybutane-2',3'-diyl)-1-thio-α-L-rhamnopyranoside | 877606-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-O-(2',3'-diethoxybutane-2',3'-diyl)-1-thio-α-L-rhamnopyranoside
• CAS: 877606-73-0
• 化学式: C₄₃H₅₈O₁₁S
• 分子量: 782.993
• InChiKey: RQSWKHXFJBPQKQ-ZRNWHWKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  55.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-O-(2',3'-diethoxybutane-2',3'-diyl)-1-thio-α-L-rhamnopyranoside 在 sodium tetrahydroborate 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3S,4aS,5S,7S,8R,8aR)-2,3-diethoxy-7-ethylsulfanyl-2,3,5-trimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-yloxy)-tetrahydro-pyran-3-ol
  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 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4-O-(2',3'-diethoxybutane-2',3'-diyl)-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