28-O-tert-butyldiphenylsilylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranoside | 1049318-92-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 28-O-tert-butyldiphenylsilylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranoside
• CAS: 1049318-92-4
• 化学式: C₈₁H₁₀₂O₁₃Si
• 分子量: 1311.78
• InChiKey: FVKYCRDPAQRKNJ-GFSKLNQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.29
• 重原子数：
  95.0
• 可旋转键数：
  16.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  28-O-tert-butyldiphenylsilylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到betulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues

  摘要：

  A concise synthesis of naturally occurring betulinic acid saponins bearing an alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside moiety at the C-3 position is described. Betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[ -D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside isolated from Pulsatilla koreana and 28-O-beta-D-glucopyranosyl betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-a-L-arabinopyranoside isolated from Schefflera rotundifolia were easily synthesized for the first time using a stepwise glycosidation approach. The overall syntheses involved eight linear steps starting from allyl betulinate and commercially available L-arabinose, L-rhamnose and D-glucose. The syntheses of betulin and betulinic acid O-glycoside analogues containing an alpha-L-arabinose moiety are also reported. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.029
• 作为产物：
  描述：

  28-O-tert-butyldiphenylsilylbetulin 3β-O-3,4-O-isopropylidene-α-L-arabinopyranoside 、 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 2.17h， 以78%的产率得到28-O-tert-butyldiphenylsilylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-O-isopropylidene-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues

  摘要：

  A concise synthesis of naturally occurring betulinic acid saponins bearing an alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside moiety at the C-3 position is described. Betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[ -D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside isolated from Pulsatilla koreana and 28-O-beta-D-glucopyranosyl betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-a-L-arabinopyranoside isolated from Schefflera rotundifolia were easily synthesized for the first time using a stepwise glycosidation approach. The overall syntheses involved eight linear steps starting from allyl betulinate and commercially available L-arabinose, L-rhamnose and D-glucose. The syntheses of betulin and betulinic acid O-glycoside analogues containing an alpha-L-arabinose moiety are also reported. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.029