(R)-4-((3aS,5aR,5bS,7aR,8R,10aS,10bS,11R,12bR)-11-Benzyloxymethoxy-5a,7a-dimethyl-2-oxo-hexadecahydro-1,3-dioxa-2λ4-thia-dicyclopenta[a,i]phenathren-8-yl)-pentanoic acid methyl ester | 610313-26-3

• 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: (R)-4-((3aS,5aR,5bS,7aR,8R,10aS,10bS,11R,12bR)-11-Benzyloxymethoxy-5a,7a-dimethyl-2-oxo-hexadecahydro-1,3-dioxa-2λ4-thia-dicyclopenta[a,i]phenathren-8-yl)-pentanoic acid methyl ester
• 英文别名: (R)-4-((3aS,5aR,5bS,7aR,8R,10aS,10bS,11R,12bR)-11-Benzyloxymethoxy-5a,7a-dimethyl-2-oxo-hexadecahydro-1,3-dioxa-2λ⁴-thia-dicyclopenta[a,i]phenathren-8-yl)-pentanoic acid methyl ester
• CAS: 610313-26-3
• 化学式: C₃₃H₄₈O₇S
• 分子量: 588.806
• InChiKey: BZBOOTMAHCYVOF-XZYNUDJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((3aS,5aR,5bS,7aR,8R,10aS,10bS,11R,12bR)-11-Benzyloxymethoxy-5a,7a-dimethyl-2-oxo-hexadecahydro-1,3-dioxa-2λ4-thia-dicyclopenta[a,i]phenathren-8-yl)-pentanoic acid methyl ester 在 吡啶 、 2,4,6-三甲基吡啶 、 lead(IV) acetate 、 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 三甲基氯硅烷 、 phosphate buffer 、 pyridine-SO3 complex 、 硫酸 、 potassium tert-butylate 、 碘 、 caesium carbonate 、 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 、 乙腈 、 叔丁醇 为溶剂， 反应 38.41h， 生成 C₂₇H₄₄S₂O₁₀(C₈H₈O)2^(2-)*2Na⁽¹⁺⁾
  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：

  methyl 7α-benzyloxymethoxy-3β,4β-dihydroxycholan-24-oate 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (R)-4-((3aS,5aR,5bS,7aR,8R,10aS,10bS,11R,12bR)-11-Benzyloxymethoxy-5a,7a-dimethyl-2-oxo-hexadecahydro-1,3-dioxa-2λ4-thia-dicyclopenta[a,i]phenathren-8-yl)-pentanoic acid methyl ester
  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