(2S)-4-<(tert-Butyldiphenylsilyl)oxy>-2-hydroxybutyl 2'-naphthalenesulfonate | 153011-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-4-<(tert-Butyldiphenylsilyl)oxy>-2-hydroxybutyl 2'-naphthalenesulfonate
• 英文别名: (2S)-4-[(tert-Butyldiphenylsilyl)oxy]-2-hydroxybutyl 2'-naphthalenesulfonate；[(2S)-4-[tert-butyl(diphenyl)silyl]oxy-2-hydroxybutyl] naphthalene-2-sulfonate
• CAS: 153011-61-1
• 化学式: C₃₀H₃₄O₅SSi
• 分子量: 534.748
• InChiKey: CRXJKVRHGPEEFW-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-4-<(tert-Butyldiphenylsilyl)oxy>-2-hydroxybutyl 2'-naphthalenesulfonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以94%的产率得到(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol
  参考文献：
  名称：

  Total synthesis of (-)-tetrahydrolipstatin

  摘要：

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.

  DOI：

  10.1021/jo00079a022
• 作为产物：
  描述：

  Methyl (2S)-4-<(tert-butyldiphenylsilyl)oxy>-2-hydroxybutyrate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 dimethyl sulfide borane 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2S)-4-<(tert-Butyldiphenylsilyl)oxy>-2-hydroxybutyl 2'-naphthalenesulfonate
  参考文献：
  名称：

  Total synthesis of (-)-tetrahydrolipstatin

  摘要：

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.

  DOI：

  10.1021/jo00079a022

文献信息

• Total synthesis of (-)-tetrahydrolipstatin
  作者：Stephen Hanessian、Ashok Tehim、Ping Chen

  DOI：10.1021/jo00079a022

  日期：1993.12

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.