Benzoic acid (3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-benzyloxymethoxy-4-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester | 753488-67-4

• 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: Benzoic acid (3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-benzyloxymethoxy-4-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
• CAS: 753488-67-4
• 化学式: C₄₀H₅₄O₇
• 分子量: 646.865
• InChiKey: VRMDYPGKDUMNGL-UMLPQKSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-benzyloxymethoxy-4-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 2,4,6-三甲基吡啶 、 lead(IV) acetate 、 正丁基锂 、 三甲基氯硅烷 、 potassium tert-butylate 、 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 27.75h， 生成 (25R)-4β,7α-dibenzyloxymethoxy-5α-cholest-23-ene-3α,26-diol 3α-benzoate
  参考文献：
  名称：

  Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; an example of nanomolar-level structure elucidation of novel natural compound

  摘要：

  A sperm-activating and attracting factor (SAAF) was isolated from the eggs of the ascidian Ciona intestinalis, and its structure was deduced with only approximately 4 mug of the specimen. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 16 steps. Comparison between synthetic and natural compounds led to the unambiguous structure determination of SAAF to be (3R, 4R, 7R, 25S)-3,4,7,26-tetrahydroxycholestane-3,26-disulfate. The synthetic pure specimen was also utilized to confirm that both sperm-activation and attraction were elicited by a single compound. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.075
• 作为产物：
  描述：

  甲基7alpha-羟基-3-氧代胆烷酸酯 在 氯化亚砜 、 potassium tert-butylate 、 氧气 、 sodium cyanoborohydride 、 caesium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 Benzoic acid (3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-benzyloxymethoxy-4-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Synthesis of endogenous sperm-activating and attracting factor isolated from ascidian Ciona intestinalis

  摘要：

  A chemoattractant candidate named sperm-activating and attracting factor (SAAF) from the eggs of ascidian Ciona intestinalis, was synthesized from chenodeoxycholic acid in 16 steps. The present synthesis led to the unambiguous structure determination of SAAF to be (3R,4R, 7R,25 S)- 3,4,7,26-tetrahydroxycholestane- 3,26-di sulfate. The synthetic pure specimen was also used to confirm the dual sperm-activating and attracting activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01598-3