{(2S,3R)-3-[(1R,2S,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-oxiranyl}-methanol | 236390-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(2S,3R)-3-[(1R,2S,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-oxiranyl}-methanol
• CAS: 236390-92-4
• 化学式: C₁₇H₃₆O₅Si
• 分子量: 348.555
• InChiKey: PIUJXFAGNMSAAM-RBGFHDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.45
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(2S,3R)-3-[(1R,2S,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-oxiranyl}-methanol 在 CuCN 作用下， 生成 (2R,3S,5S,6R)-1,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3,5-bis-methoxymethoxy-2,4,6-trimethyl-heptane
  参考文献：
  名称：

  Synthesis of a syn,syn,syn,syn-Stereopentad Precursor of the Marine Sponge Polyketide Callystatin A

  摘要：

  A C13-22 syn,syn,syn,syn-stereopentad precursor of the cytotoxic polyketide callystatin A has been prepared. The synthesis involved BF3-promoted addition of the (M)-allenylstannane 28 to the alpha-methyl-beta-OTBS aldehyde 8 to afford the syn,syn adduct homopropargylic alcohol 29. Protection as the cyclic anisylidene acetal 31 and reduction of the acetylenic triple bond with Red-Al gave the (E)-allylic alcohol 32. This was subjected to Sharpless asymmetric epoxidation and subsequent treatment with an ethylcopper reagent to yield diol 34; hydrogenolysis of the derived tosylate 37 with LiBEt3H afforded 38. Acetal hydrogenolysis with DIBAl-H and oxidation yielded aldehyde 40 which was subjected to Horner-Emmons homologation to afford ester 41. This ester was converted to ester 44, an intermediate in the Kobayashi synthesis, with which it was found to be identical.

  DOI：

  10.1021/jo9902143
• 作为产物：
  描述：

  (Z)-(2R,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-en-3-ol 在 正丁基锂 、 一溴化碘 、 碳酸氢钠 、 potassium carbonate 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 {(2S,3R)-3-[(1R,2S,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-oxiranyl}-methanol
  参考文献：
  名称：

  Synthesis of a syn,syn,syn,syn-Stereopentad Precursor of the Marine Sponge Polyketide Callystatin A

  摘要：

  A C13-22 syn,syn,syn,syn-stereopentad precursor of the cytotoxic polyketide callystatin A has been prepared. The synthesis involved BF3-promoted addition of the (M)-allenylstannane 28 to the alpha-methyl-beta-OTBS aldehyde 8 to afford the syn,syn adduct homopropargylic alcohol 29. Protection as the cyclic anisylidene acetal 31 and reduction of the acetylenic triple bond with Red-Al gave the (E)-allylic alcohol 32. This was subjected to Sharpless asymmetric epoxidation and subsequent treatment with an ethylcopper reagent to yield diol 34; hydrogenolysis of the derived tosylate 37 with LiBEt3H afforded 38. Acetal hydrogenolysis with DIBAl-H and oxidation yielded aldehyde 40 which was subjected to Horner-Emmons homologation to afford ester 41. This ester was converted to ester 44, an intermediate in the Kobayashi synthesis, with which it was found to be identical.

  DOI：

  10.1021/jo9902143