(R)-3-(tert-butyldimethylsilanyloxy)-3-((1R,2R)-2-(trityloxymethyl)cyclopropyl)propanal | 1029316-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (R)-3-(tert-butyldimethylsilanyloxy)-3-((1R,2R)-2-(trityloxymethyl)cyclopropyl)propanal
• CAS: 1029316-83-3
• 化学式: C₃₂H₄₀O₃Si
• 分子量: 500.753
• InChiKey: GCQVQXKHEVQTAX-AWJLRTIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-butyldimethylsilanyloxy)-3-((1R,2R)-2-(trityloxymethyl)cyclopropyl)propanal 、 二溴甲烷 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 以58.5 mg的产率得到tert-butyldimethyl-((R)-1-((1R,2R)-2-(trityloxymethyl)cyclopropyl)but-3-enyloxy)silane
  参考文献：
  名称：

  Solandelactones A，B，E和F的全合成开发了串联Petasis-Claisen酸化策略

  摘要：

  Solandelactones A, B, E, and F were synthesized using Nozaki-Hiyania-Kishi coupling of iododiene 13 with aldehydes 14 and 99 obtained by oxidation of alcohols 92 and 94. Key steps in the synthesis of 92 and 94 were (i) a Nagao asymmetric acetate aldol reaction of aldehyde 77 with thionothiazolidine 78 to set in place an alcohol that becomes the (7S) lactone center of solandelactones, (ii) a Simmons-Smith cyclopropanation of 80 directed by this alcohol, and (iii) Petasis methylenation of cyclic carbonate 90 in tandem with a Claisen rearrangement that generates the octenalactone portion of solandelactones. Synthesis of solandelactones A, B, E, and F confirmed their gross structure and absolute configuration at C7, 8, 10, and 14 but showed that alcohol configuration at C11 must be reversed in pairs, A/B and E/F, from the previous assignment made to these hydroid metabolites. Thus, solandelactones A and B are correctly represented by 2 and 1, respectively, whereas solandelactones E and F are 6 and 5. A biogenesis of solandelactones is proposed for these C(22) oxylipins that parallels a hypothesis put forward previously to explain the origin of C(20) cyclopropane-containing algal products.

  DOI：

  10.1021/jo800335g
• 作为产物：
  描述：

  (1R,2R)-1-trityloxymethyl-2-[1-(R)-tert-butyldimethylsilanyloxy-4-hydroxypropyl]cyclopropane 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-3-(tert-butyldimethylsilanyloxy)-3-((1R,2R)-2-(trityloxymethyl)cyclopropyl)propanal
  参考文献：
  名称：

  Solandelactones A，B，E和F的全合成开发了串联Petasis-Claisen酸化策略

  摘要：

  Solandelactones A, B, E, and F were synthesized using Nozaki-Hiyania-Kishi coupling of iododiene 13 with aldehydes 14 and 99 obtained by oxidation of alcohols 92 and 94. Key steps in the synthesis of 92 and 94 were (i) a Nagao asymmetric acetate aldol reaction of aldehyde 77 with thionothiazolidine 78 to set in place an alcohol that becomes the (7S) lactone center of solandelactones, (ii) a Simmons-Smith cyclopropanation of 80 directed by this alcohol, and (iii) Petasis methylenation of cyclic carbonate 90 in tandem with a Claisen rearrangement that generates the octenalactone portion of solandelactones. Synthesis of solandelactones A, B, E, and F confirmed their gross structure and absolute configuration at C7, 8, 10, and 14 but showed that alcohol configuration at C11 must be reversed in pairs, A/B and E/F, from the previous assignment made to these hydroid metabolites. Thus, solandelactones A and B are correctly represented by 2 and 1, respectively, whereas solandelactones E and F are 6 and 5. A biogenesis of solandelactones is proposed for these C(22) oxylipins that parallels a hypothesis put forward previously to explain the origin of C(20) cyclopropane-containing algal products.

  DOI：

  10.1021/jo800335g