allyl betulinate 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside | 1049318-96-8

• 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: allyl betulinate 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside
• 英文别名: prop-2-enyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-4-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 1049318-96-8
• 化学式: C₉₉H₁₀₈O₂₃
• 分子量: 1665.93
• InChiKey: PFZIKGQLEVSANA-ALXINYRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20
• 重原子数：
  122
• 可旋转键数：
  33
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  286
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  allyl betulinate 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside 在 四(三苯基膦)钯 四氢吡咯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-4-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
  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：

  allyl betulinate 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 4 A molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 以50%的产率得到allyl betulinate 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-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