(3R,5S,7R,8R,9S,10R,2'S,3'S)-10-Benzyloxy-7-benzyloxymethyl-8,9-di-O-(2',3'-dimethoxy-2',3'-diyl)-3-hydroxy-1,6-dioxaspiro[4.5]decane | 302332-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3R,5S,7R,8R,9S,10R,2'S,3'S)-10-Benzyloxy-7-benzyloxymethyl-8,9-di-O-(2',3'-dimethoxy-2',3'-diyl)-3-hydroxy-1,6-dioxaspiro[4.5]decane
• CAS: 302332-07-6
• 化学式: C₂₉H₃₈O₉
• 分子量: 530.615
• InChiKey: DLAJEXGPUKWGGE-BKJIVZHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  94.07
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (3R,5S,7R,8R,9S,10R,2'S,3'S)-10-Benzyloxy-7-benzyloxymethyl-8,9-di-O-(2',3'-dimethoxy-2',3'-diyl)-3-hydroxy-1,6-dioxaspiro[4.5]decane 在 吡啶 、 4-二甲氨基吡啶 、 3 A molecular sieve 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 (3R,5S,7R,8R,9S,10R,2'S,3'S)-10-Benzyloxy-7-benzyloxymethyl-8,9-di-O-(2',3'-dimethoxy-2',3'-diyl)-3-hydroxy-1,6-dioxaspiro[4.5]decane (R)-Mosher ester
  参考文献：
  名称：

  Spirophostins: Conformationally Restricted Analogues of Adenophostin A

  摘要：

  The synthesis, biological evaluation, and molecular modeling of two conformationally restricted analogues of adenophostin A (1), denominated as spirophostin (3R)-10 and (3S)-11, as novel ligands for the D-myo-inositol 1,4,5-trisphosphate receptor (IP3R), is presented, These diastereoisomeric Spiroketals are synthesized by spiroketalization of D-glucose derivatives (2S)-15 and (2R)-16, separation of the protected isomers (3R)-19 and (3S)-20, followed by phosphorylation and deprotection, The spirophostins (3R)-10 and (3S)-11 display comparable biological activity, with a H-3-IP3-displacing and Ca2+-releasing potency less than IP3 and adenophostin A.

  DOI：

  10.1002/1521-3765(20000804)6:15<2696::aid-chem2696>3.0.co;2-y
• 作为产物：
  描述：

  (2'S,3'S)-2,6-Di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-D-glucono-1,5-lactone 在 potassium osmate(VI) 、 N-甲基吲哚酮 、 camphor-10-sulfonic acid 、 水 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 19.5h， 生成 (3R,5S,7R,8R,9S,10R,2'S,3'S)-10-Benzyloxy-7-benzyloxymethyl-8,9-di-O-(2',3'-dimethoxy-2',3'-diyl)-3-hydroxy-1,6-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Spirophostins: Conformationally Restricted Analogues of Adenophostin A

  摘要：

  The synthesis, biological evaluation, and molecular modeling of two conformationally restricted analogues of adenophostin A (1), denominated as spirophostin (3R)-10 and (3S)-11, as novel ligands for the D-myo-inositol 1,4,5-trisphosphate receptor (IP3R), is presented, These diastereoisomeric Spiroketals are synthesized by spiroketalization of D-glucose derivatives (2S)-15 and (2R)-16, separation of the protected isomers (3R)-19 and (3S)-20, followed by phosphorylation and deprotection, The spirophostins (3R)-10 and (3S)-11 display comparable biological activity, with a H-3-IP3-displacing and Ca2+-releasing potency less than IP3 and adenophostin A.

  DOI：

  10.1002/1521-3765(20000804)6:15<2696::aid-chem2696>3.0.co;2-y