(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfenyl]-2-hexanol | 537035-61-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfenyl]-2-hexanol
• 英文别名: tert-butyl N-[(2R,3S)-2-hydroxy-5-methyl-1-(4-methylphenyl)sulfanylhexan-3-yl]carbamate
• CAS: 537035-61-3
• 化学式: C₁₉H₃₁NO₃S
• 分子量: 353.526
• InChiKey: FEVKSUPTMYVYFI-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfenyl]-2-hexanol 在 trimethoxonium tetrafluoroborate 、 potassium carbonate 作用下， 以 Petroleum ether 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 以63%的产率得到(R)-1-[(S)-1-(tert-butoxycarbonylamino)-3-methylbutyl]oxirane
  参考文献：
  名称：

  A stereodivergent approach to syn- and anti-β-hydroxy-γ-amino acids. Enantioselective synthesis of N-Boc-statine and N-Boc-3-epistatine mediated by sulfoxides

  摘要：

  Asymmetric syntheses of the syn- and anti-stereoisomers of N-Boc statine, based on the stereodivergent reduction of a single sulfoxide 5, derived from N-Boc-L-leucine, are reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00819-4
• 作为产物：
  描述：

  (2R,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfinyl]-2-hexanol 在 盐酸 、 titanium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以90%的产率得到(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-5-methyl-1-[(4-methylphenyl)sulfenyl]-2-hexanol
  参考文献：
  名称：

  A stereodivergent approach to syn- and anti-β-hydroxy-γ-amino acids. Enantioselective synthesis of N-Boc-statine and N-Boc-3-epistatine mediated by sulfoxides

  摘要：

  Asymmetric syntheses of the syn- and anti-stereoisomers of N-Boc statine, based on the stereodivergent reduction of a single sulfoxide 5, derived from N-Boc-L-leucine, are reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00819-4

文献信息

• A stereodivergent approach to syn- and anti-β-hydroxy-γ-amino acids. Enantioselective synthesis of N-Boc-statine and N-Boc-3-epistatine mediated by sulfoxides
  作者：Francisco Yuste、Angel Dı́az、Benjamı́n Ortiz、Rubén Sánchez-Obregón、Fernando Walls、José L.Garcı́a Ruano

  DOI：10.1016/s0957-4166(02)00819-4

  日期：2003.3

  Asymmetric syntheses of the syn- and anti-stereoisomers of N-Boc statine, based on the stereodivergent reduction of a single sulfoxide 5, derived from N-Boc-L-leucine, are reported. (C) 2003 Elsevier Science Ltd. All rights reserved.