(1R,2S)-1-[[(1S,2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl]sulfanyl]-1-ethoxy-2-phenylbut-3-en-2-ol | 682352-21-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S)-1-[[(1S,2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl]sulfanyl]-1-ethoxy-2-phenylbut-3-en-2-ol
• CAS: 682352-21-2
• 化学式: C₂₈H₄₆O₃SSi
• 分子量: 490.823
• InChiKey: NRVBKTHGISECCB-ITFZYEJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-[[(1S,2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl]sulfanyl]-1-ethoxy-2-phenylbut-3-en-2-ol 在 N-氯代丁二酰亚胺 、 silver nitrate 、 sodium tetrahydroborate 作用下， 生成 (S)-(-)-2-phenylbut-3-ene-1,2-diol 、 3-丁烯-1,2-二醇,2-苯基-,(2R)- 、
  参考文献：
  名称：

  New S,O-acetals from (1R)-(−)-myrtenal as chiral auxiliaries in nucleophilic additions

  摘要：

  Treatment of hydroxythiol 4 with alpha,alpha-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4. 92%, yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99%, yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.046
• 作为产物：
  描述：

  10-hydroxyisopinocampheylthiol 在 咪唑 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2S)-1-[[(1S,2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl]sulfanyl]-1-ethoxy-2-phenylbut-3-en-2-ol
  参考文献：
  名称：

  New S,O-acetals from (1R)-(−)-myrtenal as chiral auxiliaries in nucleophilic additions

  摘要：

  Treatment of hydroxythiol 4 with alpha,alpha-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4. 92%, yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99%, yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.046

文献信息

• New S,O-acetals from (1R)-(−)-myrtenal as chiral auxiliaries in nucleophilic additions
  作者：Luis Chacón-Garcı́a、Selene Lagunas-Rivera、Salvador Pérez-Estrada、M. Elena Vargas-Dı́az、Pedro Joseph-Nathan、Joaquı́n Tamariz、L.Gerardo Zepeda

  DOI：10.1016/j.tetlet.2004.01.046

  日期：2004.3

  Treatment of hydroxythiol 4 with alpha,alpha-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4. 92%, yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99%, yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er). (C) 2004 Elsevier Ltd. All rights reserved.