cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester | 157020-35-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: (Z)-7-[(2R,4R)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-phenyl-1,3-thiazolidin-4-yl]hept-6-enoic acid
• CAS: 157020-35-4
• 化学式: C₂₁H₂₉NO₄S
• 分子量: 391.532
• InChiKey: LVRNODHEKZCLEG-NODARJAWSA-N

物化性质

• 沸点：
  547.5±50.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester 在 吡啶 、 盐酸 、 sodium azide 、 buffer: citric acid pH 4 、 硫酸 、 氨 、 sodium 、 sodium cyanoborohydride 、 碳酸氢钠 、 magnesium sulfate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二氯磷酸苯酯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 47.67h， 生成 <3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester
  参考文献：
  名称：

  Novel Enantioselective Syntheses of (+)-Biotin

  摘要：

  Two conceptually attractive enantioselective syntheses of(+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide. The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of(+)-biotin 16a and 17a. The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b. Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.

  DOI：

  10.1021/jo00107a009
• 作为产物：
  描述：

  6-溴己酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 17.5h， 生成 cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Novel Enantioselective Syntheses of (+)-Biotin

  摘要：

  Two conceptually attractive enantioselective syntheses of(+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide. The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of(+)-biotin 16a and 17a. The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b. Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.

  DOI：

  10.1021/jo00107a009

文献信息

• A novel enantioselective synthesis of (+)-biotin
  作者：Frederik D. Deroose、Pierre J. De Clercq

  DOI：10.1016/s0040-4039(00)77187-5

  日期：1994.4

  attractive enantioselective 12-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cycloaddition sequence involving as key-steps (i) the macrothiolactonisation of acid 3 to Z-olefin 4, (ii) the thermolysis of the ene carbamoyl azide 5 in water with direct formation of a mixture of the benzylated derivatives of (+)-biotin 6a and 6b.

  据报道，基于分子内的1,3-偶极环加成序列，L-半胱氨酸具有（+）-生物素的概念上有吸引力的对映选择性12步合成步骤，该步骤涉及（i）酸3至Z-烯烃4的大硫醇内酯化， （ii）烯氨基甲酰基叠氮化物5在水中的热分解，直接形成（+）-生物素6a和6b的苄基化衍生物的混合物。
• Novel Enantioselective Syntheses of (+)-Biotin
  作者：Frederik D. Deroose、Pierre J. De Clercq

  DOI：10.1021/jo00107a009

  日期：1995.1

  Two conceptually attractive enantioselective syntheses of(+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide. The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of(+)-biotin 16a and 17a. The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b. Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.