(2S,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanol | 310450-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanol
• 英文别名: tert-butyl N-[(2S,3S)-3-hydroxy-4-[(R)-(4-methylphenyl)sulfinyl]butan-2-yl]carbamate
• CAS: 310450-37-4
• 化学式: C₁₆H₂₅NO₄S
• 分子量: 327.445
• InChiKey: ZKXCFTXCEGRBCU-QEXXDVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanol 在 镍 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到2-甲基-2-丙基[(2S,3R)-3-羟基-2-丁烷基]氨基甲酸酯
  参考文献：
  名称：

  Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides

  摘要：

  Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easily synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-keto sulfoxides (easily synthesized from readily available N-Boc amino eater hydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed by hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and final hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00264-0
• 作为产物：
  描述：

  BOC-L-丙氨酸甲酯 在 二异丁基氢化铝 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 (2S,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanol
  参考文献：
  名称：

  Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides

  摘要：

  Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easily synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-keto sulfoxides (easily synthesized from readily available N-Boc amino eater hydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed by hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and final hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00264-0

文献信息

• Enantioselective synthesis of α-hydroxy-β-amino acids from α-amino acids mediated by sulfoxides
  作者：Rubén Sánchez-Obregón、Fernando Salgado、Benjamín Ortiz、Eduardo Díaz、Francisco Yuste、Fernando Walls、José L. García Ruano

  DOI：10.1016/j.tet.2007.07.072

  日期：2007.10

  available (S)-alanine derivatives is reported. The key step of the synthetic sequence is the conversion of γ-amino sulfoxides into γ-amino alcohols by treatment with TFAA and sym-collidine. The efficiency of this non-oxidative Pummerer reaction (NOPR) is dependent on the stereochemistry of the starting sulfoxide.

  据报道，由市售的（S）-丙氨酸衍生物合成了光学纯的（2 S，3 S）-和（2 R，3 S）-3-氨基-2-羟基丁酸。合成顺序的关键步骤是γ氨基亚砜的通过用TFAA和治疗转化为γ-氨基醇符号-collidine。这种非氧化性Pummerer反应（NOPR）的效率取决于起始亚砜的立体化学。
• Synthesis of enantiomerically pure 2-amino alcohols from amino acids mediated by sulfoxides
  作者：Francisco Yuste、Benjamin Ortiz、Alejandra Carrasco、Martha Peralta、Leticia Quintero、Rubén Sánchez-Obregón、Fernando Walls、José L Garcı́a Ruano

  DOI：10.1016/s0957-4166(00)00264-0

  日期：2000.8

  Enantiomerically pure (R-1,S-2)- and (S-1,S-2)-2-amino alcohols can be easily synthesized by stereodivergent reduction of alpha'-(N-Boc)amino beta-keto sulfoxides (easily synthesized from readily available N-Boc amino eater hydrochlorides) with DIBAH (clr 82-92%) and DIBAH/ZnBr2 (de 80%), followed by hydrogenolysis of the C-S bond of the resulting hydroxy sulfoxides and final hydrolysis of the N-Boc protecting group. (C) 2000 Elsevier Science Ltd. All rights reserved.