(4R)-N-benzyl-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxamide | 159114-05-3

• 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: (4R)-N-benzyl-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxamide
• CAS: 159114-05-3
• 化学式: C₂₀H₂₈N₂O₂S
• 分子量: 360.521
• InChiKey: ZQQURORKFODMRG-ROUUACIJSA-N

物化性质

• 沸点：
  587.7±50.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-N-benzyl-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxamide 在 钯 六甲基磷酰三胺 、 cesium hydroxide 、 氢溴酸 、 氢气 、 potassium hydride 、 对甲苯磺酸 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 为溶剂， 25.0~40.0 ℃ 、1.01 MPa 条件下， 反应 35.17h， 生成 (+)-deoxybiotin
  参考文献：
  名称：

  Diastereoface Discrimination in the Addition of Acetylide to a Chiral Aldehyde, Leading to a Synthesis of (+)-Deoxybiotin in Enantiomerically Pure Form Starting from L-Cysteine

  摘要：

  Complete diastereofacial discrimination was observed upon addition of the chlorozinc acetylide derived from 1-hexyne to a chiral aldehyde prepared from L-cysteine. The addition product was used in a short synthesis of (+)-deoxybiotin, a precursor of (+)-biotin, which was produced in enantiomerically pure form in 12 steps, starting from L-cysteine.

  DOI：

  10.1021/jo00099a009
• 作为产物：
  描述：

  tert-butyl (4R)-4-formyl-2,2-dimethylthiazolidine-3-carboxylate 在 吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 35.0h， 生成 (4R)-N-benzyl-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxamide
  参考文献：
  名称：

  Diastereoface Discrimination in the Addition of Acetylide to a Chiral Aldehyde, Leading to a Synthesis of (+)-Deoxybiotin in Enantiomerically Pure Form Starting from L-Cysteine

  摘要：

  Complete diastereofacial discrimination was observed upon addition of the chlorozinc acetylide derived from 1-hexyne to a chiral aldehyde prepared from L-cysteine. The addition product was used in a short synthesis of (+)-deoxybiotin, a precursor of (+)-biotin, which was produced in enantiomerically pure form in 12 steps, starting from L-cysteine.

  DOI：

  10.1021/jo00099a009

文献信息

• Diastereoface Discrimination in the Addition of Acetylide to a Chiral Aldehyde, Leading to a Synthesis of (+)-Deoxybiotin in Enantiomerically Pure Form Starting from L-Cysteine
  作者：Tamotsu Fujisawa、Michiharu Nagai、Yoshihiro Koike、Makoto Shimizu

  DOI：10.1021/jo00099a009

  日期：1994.10

  Complete diastereofacial discrimination was observed upon addition of the chlorozinc acetylide derived from 1-hexyne to a chiral aldehyde prepared from L-cysteine. The addition product was used in a short synthesis of (+)-deoxybiotin, a precursor of (+)-biotin, which was produced in enantiomerically pure form in 12 steps, starting from L-cysteine.