octyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside | 877606-69-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: (3aR,4S,6S,7S,7aR)-4-[[(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-octoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 877606-69-4
• 化学式: C₂₆H₄₆O₉
• 分子量: 502.646
• InChiKey: IMXVAKRNZQXTIM-QGAUAZOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  octyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 、 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 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到
  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：

  octyl 2,3-isopropylidene-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 octyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-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

文献信息

• Synthesis of the pentasaccharide repeating unit of latosillan
  作者：Yuxia Hua、Junjun Xiao、Yingshen Huang、Yuguo Du

  DOI：10.1016/j.carres.2005.11.007

  日期：2006.2

  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.