(2S,3R)-3-hydroxy-3-methyl-1-(p-tolylsulfonyl)-pyrrolidine-2-carboxylic acid | 794567-08-1

• 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,3R)-3-hydroxy-3-methyl-1-(p-tolylsulfonyl)-pyrrolidine-2-carboxylic acid
• 英文别名: (2R,3R)-(-)-3-hydroxy-3-methyl-1-(toluene-4-sulfonyl)pyrrolidine-2-carboxylic acid；(2S,3R)-3-hydroxy-3-methyl-1-(4-methylphenyl)sulfonylpyrrolidine-2-carboxylic acid
• CAS: 794567-08-1
• 化学式: C₁₃H₁₇NO₅S
• 分子量: 299.348
• InChiKey: RITJXPLQBHCPNV-DGCLKSJQSA-N

物化性质

• 沸点：
  511.9±60.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-hydroxy-3-methyl-1-(p-tolylsulfonyl)-pyrrolidine-2-carboxylic acid 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 以914 mg的产率得到5-methyl-2-tosyl-6-oxa-2-azabicyclo[3.2.0]heptan-7-one
  参考文献：
  名称：

  Organocatalytic Synthesis of (2S,3R)-3-Hydroxy-3-methyl-proline (OHMePro), a Component of Polyoxypeptins, and Relatives Using OHMePro Itself as a Catalyst

  摘要：

  An efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (OHMePro), a component of polyoxypeptins, and relatives was achieved, in which an intramolecular asymmetric aldol reaction of the ketoaldehyde using OHMePro itself as an organocatalyst constitutes a key step.

  DOI：

  10.1021/ol0706004
• 作为产物：
  描述：

  N-allyl-4-methyl-N-(3-oxobutyl)benzenesulfonamide 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 phosphate buffer 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 14.0h， 生成 (2S,3R)-3-hydroxy-3-methyl-1-(p-tolylsulfonyl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Organocatalytic Synthesis of (2S,3R)-3-Hydroxy-3-methyl-proline (OHMePro), a Component of Polyoxypeptins, and Relatives Using OHMePro Itself as a Catalyst

  摘要：

  An efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (OHMePro), a component of polyoxypeptins, and relatives was achieved, in which an intramolecular asymmetric aldol reaction of the ketoaldehyde using OHMePro itself as an organocatalyst constitutes a key step.

  DOI：

  10.1021/ol0706004

文献信息

• A Short-Step Synthesis of (2<i>S</i>,3<i>R</i>)-3-Hydroxy-3-methylproline, a Component of Polyoxypeptins, Using a Tandem Michael–Aldol Reaction and Optical Resolution
  作者：Kazuishi Makino、Tatsuya Suzuki、Yasumasa Hamada

  DOI：10.1246/bcsj.77.1649

  日期：2004.9

  A short-step synthesis of (2S,3R)-3-hydroxy-3-methylproline, a component of polyoxypeptins, using a tandem Michael–aldol reaction followed by its optical resolution using (−)-cinchonidine has been achieved.

  （2S，3R）-3-羟基-3-甲基脯氨酸（一种多肽的成分）的短步骤合成已经实现，该合成使用串联迈克尔-阿尔多反应，然后使用（-）-辛可尼定进行光学拆分。
• Asymmetric Synthesis of α-Amino 1,3-Dithioketals from Sulfinimines (<i>N</i>-Sulfinyl Imines). Synthesis of (2<i>S</i>,3<i>R</i>)-(−)-3-Hydroxy-3-methylproline
  作者：Franklin A. Davis、Tokala Ramachandar、Hu Liu

  DOI：10.1021/ol0485971

  日期：2004.9.1

  N-Sulfinyl alpha-amino 1,3-dithioketals are prepared in high de and good yield by treating sulfinimines with lithio-1,3-dithianes. Selective removal of the N-sulfinyl or the thioketal groups affords stable a-amino 1,3-dithioketals and N-sulfinyl alpha-amino ketones, respectively. This new sulfinimine-derived chiral building block is employed in the asymmetric synthesis of polyoxypeptin amino acid (2S,3R)-(-)-3-hydroxy-3-methylproline.
• Organocatalytic Synthesis of (2<i>S</i>,3<i>R</i>)-3-Hydroxy-3-methyl-proline (OHMePro), a Component of Polyoxypeptins, and Relatives Using OHMePro Itself as a Catalyst
  作者：Yayoi Yoshitomi、Kazuishi Makino、Yasumasa Hamada

  DOI：10.1021/ol0706004

  日期：2007.6.1

  An efficient synthesis of (2S,3R)-3-hydroxy-3-methylproline (OHMePro), a component of polyoxypeptins, and relatives was achieved, in which an intramolecular asymmetric aldol reaction of the ketoaldehyde using OHMePro itself as an organocatalyst constitutes a key step.