diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-acetyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside | 573700-82-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-acetyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate
• CAS: 573700-82-0
• 化学式: C₆₈H₉₀O₁₆Si
• 分子量: 1191.54
• InChiKey: QCAKGUIMTZXDGX-KGZUGVITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.58
• 重原子数：
  85
• 可旋转键数：
  19
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 、 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-acetyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 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86%的产率得到diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)]-3-O-acetyl-6-O-tert-butyldimethylsilyl-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：

  diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 在 咪唑 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-acetyl-6-O-tert-butyldimethylsilyl-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