tert-butyl (4R)-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxylate | 159114-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (4R)-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxylate
• CAS: 159114-01-9
• 化学式: C₁₇H₂₉NO₃S
• 分子量: 327.488
• InChiKey: MZPLVNMVSGOJJW-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxylate 在 钯 吡啶 、 六甲基磷酰三胺 、 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 48.17h， 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 、 1-己炔 在 正丁基锂 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 10.0h， 以86%的产率得到tert-butyl (4R)-4-[(1S)-1-hydroxyhept-2-ynyl]-2,2-dimethyl-1,3-thiazolidine-3-carboxylate
  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.