(3S,4S)-N-(t-butyldimethylsilyl)-3-<(1R)-1-(tert-butyldimethylsilyloxy)-ethyl>-4-<1-(hydroxy)-1-(methyl)ethyl>-azetidin-2-one | 137063-77-5

• 英文名称: (3S,4S)-N-(t-butyldimethylsilyl)-3-<(1R)-1-(tert-butyldimethylsilyloxy)-ethyl>-4-<1-(hydroxy)-1-(methyl)ethyl>-azetidin-2-one
• 英文别名: (3S,4S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(2-hydroxypropan-2-yl)azetidin-2-one
• CAS: 137063-77-5
• 化学式: C₂₀H₄₃NO₃Si₂
• 分子量: 401.737
• InChiKey: VKFIIEGFXDFUMA-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-N-(t-butyldimethylsilyl)-3-<(1R)-1-(tert-butyldimethylsilyloxy)-ethyl>-4-<1-(hydroxy)-1-(methyl)ethyl>-azetidin-2-one 在 盐酸 、 dimethyl sulfide borane 、 双氧水 、 sodium acetate 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<(R)-1-(hydroxymethyl)ethyl>-2-azetidinone
  参考文献：
  名称：

  1β-Methylthienamycin: Some stereocontrolled approaches towards the key intermediate

  摘要：

  Two stereocontrolled approaches towards a precursor of 1 beta-methyl-thienamycin, have been accomplished by involving stereospecific hydrogenation of 13 and stereoselective hydroboration oxidation of 9. The latter compounds were obtained from the easily accessible chiral building block 7. The hydroboration-oxidation approach was extended to 18 in which the optically active 1R- (1-hydroxy ethyl) side-chain was incorporated. The highly stereoselective hydroboration-oxidation reaction of 9 is explained by considering Houk's models.

  DOI：

  10.1016/s0040-4020(01)96165-4
• 作为产物：
  描述：

  [3S-[3α(S*),4β]]-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate 以 乙醚 为溶剂， 反应 2.0h， 生成 (3S,4S)-N-(t-butyldimethylsilyl)-3-<(1R)-1-(tert-butyldimethylsilyloxy)-ethyl>-4-<1-(hydroxy)-1-(methyl)ethyl>-azetidin-2-one
  参考文献：
  名称：

  1β-Methylthienamycin: Some stereocontrolled approaches towards the key intermediate

  摘要：

  Two stereocontrolled approaches towards a precursor of 1 beta-methyl-thienamycin, have been accomplished by involving stereospecific hydrogenation of 13 and stereoselective hydroboration oxidation of 9. The latter compounds were obtained from the easily accessible chiral building block 7. The hydroboration-oxidation approach was extended to 18 in which the optically active 1R- (1-hydroxy ethyl) side-chain was incorporated. The highly stereoselective hydroboration-oxidation reaction of 9 is explained by considering Houk's models.

  DOI：

  10.1016/s0040-4020(01)96165-4