28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-3-O-benzyl-6-O-trityl-β-D-glucopyranoside) | 1039373-70-0

• 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-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-3-O-benzyl-6-O-trityl-β-D-glucopyranoside)
• 英文别名: [(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-3,5-dibenzoyloxy-4-phenylmethoxy-6-(trityloxymethyl)oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1039373-70-0
• 化学式: C₁₁₀H₁₁₂O₁₉
• 分子量: 1738.09
• InChiKey: XQKNUDIGIDSZCQ-ITQWMHRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.6
• 重原子数：
  129
• 可旋转键数：
  33
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  230
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-3-O-benzyl-6-O-trityl-β-D-glucopyranoside) 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以93%的产率得到28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-β-D-glucopyranoside)
  参考文献：
  名称：

  Synthesis of Betavulgaroside III, a Representative Triterpene seco-Glycoside

  摘要：

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.

  DOI：

  10.1021/jo800669h
• 作为产物：
  描述：

  2,4-di-O-benzoyl-3-O-benzyl-6-O-trityl-α-D-glucopyranosyl trichloroacetimidate 、 oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-3-O-benzyl-6-O-trityl-β-D-glucopyranoside)
  参考文献：
  名称：

  Synthesis of Betavulgaroside III, a Representative Triterpene seco-Glycoside

  摘要：

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.

  DOI：

  10.1021/jo800669h