2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 1004771-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Rha(a1-4)[Bz(-6)]Glc2Ac3Ac(b1-6)Glc2Ac3Ac4Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1004771-46-3
• 化学式: C₅₈H₅₈Cl₃NO₂₄
• 分子量: 1259.45
• InChiKey: ADUHUKXPBNXNQL-WBMFYUPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  86
• 可旋转键数：
  30
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  316
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 、 3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-trityl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl] ester
  参考文献：
  名称：

  Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu

  摘要：

  3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. one-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.04.005
• 作为产物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside 、 三氯乙腈 在 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  从民间药中分离出二倍体三萜皂苷类黄素总皂苷II的合成狄武，Di Wu

  摘要：

  总黄酮苷II，3-O-α-L-鼠李吡喃糖基-（1-> 2）-β-D-吡喃并吡喃基果酸28-O-α-L-鼠李吡喃糖基-（1-> 4）-β -D-吡喃葡萄糖基-（1-> 6）-β-D-吡喃葡萄糖苷是从异丙基2-O-乙酰基-3,4-二-O-苯甲酰基-的结构单元中分离而来的1-硫代-β-D-吡喃吡喃糖苷，2,3,4-三-O-苯甲酰基-α-L-鼠李吡喃糖基三氯乙酰亚胺酸酯，齐墩果酸三苯甲基酯，2,3-二-O-乙酰基-6-O-苯甲酰基乙酯-1-硫代-β-D-吡喃葡萄糖苷和4-甲氧基苯基2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷。使用部分保护的硫糖基供体可大大简化目标皂苷的合成。

  DOI：

  10.1016/j.carres.2007.11.015