2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose | 573700-74-0

• 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->2)-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose
• CAS: 573700-74-0
• 化学式: C₄₁H₄₂O₁₇
• 分子量: 806.774
• InChiKey: GIVZWLZTZAUPTQ-PONLKVKTSA-N

物化性质

• 沸点：
  829.1±65.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 在 无水碳酸镉 、 camphor-10-sulfonic acid 、 氢溴酸 、 溶剂黄146 、 胍 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides

  摘要：

  Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00004-1
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose
  参考文献：
  名称：

  The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides

  摘要：

  Two representative spirostanol saponins that have the typical structure for the sugar moiety, diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranoside (gracillin) and diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (dioscin), were easily synthesized by a general approach. A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00004-1