2S,4S-methyl 2-tert-butyl-1,3-thiazolidine-3-formyl-4-methyl-4-carboxylate | 150989-21-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2S,4S-methyl 2-tert-butyl-1,3-thiazolidine-3-formyl-4-methyl-4-carboxylate
• 英文别名: methyl (2S,4S)-2-tert-butyl-3-formyl-4-methyl-1,3-thiazolidine-4-carboxylate
• CAS: 150989-21-2
• 化学式: C₁₁H₁₉NO₃S
• 分子量: 245.343
• InChiKey: PMGZJXSUJXMEKU-GZMMTYOYSA-N

物化性质

• 沸点：
  353.8±42.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2S,4S-methyl 2-tert-butyl-1,3-thiazolidine-3-formyl-4-methyl-4-carboxylate 在 盐酸 作用下， 反应 72.0h， 生成 2-甲基-L-半胱氨酸盐酸盐
  参考文献：
  名称：

  Synthesis of the thiazoline-based siderophore (S)-desferrithiocin

  摘要：

  A total synthesis of the new thiazoline-based siderophore desferrithiocin 1, isolated from Streptomyces antibioticus, is described. Thus, a concise synthesis of (S)-2-methylcysteine hydrochloride 11 is first developed based on a modification of Seebach's ''self-reproduction of chirality'' protocol using the thiazolidine intermediate 8 derived from (S)-cysteine and pivaldehyde as a key intermediate. When a solution of (S)-2-methylcysteine hydrochloride is heated with 2-cyano-3-hydroxypyridine in the presence of triethylamine, (S)-desferrithiocin is produced in 97% yield. In a similar manner, use of (R)-2-methylcysteine in a cyclocondensation with 2-cyano-3-hydroxypyridine led to (R)-desferrithiocin, in a similar yield.

  DOI：

  10.1016/s0040-4020(01)82385-1
• 作为产物：
  描述：

  4S-methyl 2-tert-butyl-1,3-thiazolidine-4-carboxylate 在 N,N-二甲基丙烯基脲 、 甲酸 、 乙酸酐 、 lithium diisopropyl amide 作用下， 反应 2.75h， 生成 2S,4S-methyl 2-tert-butyl-1,3-thiazolidine-3-formyl-4-methyl-4-carboxylate
  参考文献：
  名称：

  Synthesis of the thiazoline-based siderophore (S)-desferrithiocin

  摘要：

  A total synthesis of the new thiazoline-based siderophore desferrithiocin 1, isolated from Streptomyces antibioticus, is described. Thus, a concise synthesis of (S)-2-methylcysteine hydrochloride 11 is first developed based on a modification of Seebach's ''self-reproduction of chirality'' protocol using the thiazolidine intermediate 8 derived from (S)-cysteine and pivaldehyde as a key intermediate. When a solution of (S)-2-methylcysteine hydrochloride is heated with 2-cyano-3-hydroxypyridine in the presence of triethylamine, (S)-desferrithiocin is produced in 97% yield. In a similar manner, use of (R)-2-methylcysteine in a cyclocondensation with 2-cyano-3-hydroxypyridine led to (R)-desferrithiocin, in a similar yield.

  DOI：

  10.1016/s0040-4020(01)82385-1

文献信息

• 一种拉格唑拉类似物，其制备方法及其应用
  申请人：中国科学院广州生物医药与健康研究院

  公开号：CN103601742B

  公开（公告）日：2016-01-20

  本发明公开了一种如式1所示的具有烷基二硫醚侧链的拉格唑拉类似物、其制备方法及其应用，本发明的化合物具有较高的抗肿瘤活性和选择性，可用于发展抗肿瘤药物，且原料廉价易得，制备方法简易，是一种适于发展成工业化生产的方法。式1，其中R为C1～C8烷基。
• Synthesis of the thiazoline-based siderophore (S)-desferrithiocin
  作者：Gerard C. Mulqueen、Gerald Pattenden、Donald A. Whiting

  DOI：10.1016/s0040-4020(01)82385-1

  日期：1993.6

  A total synthesis of the new thiazoline-based siderophore desferrithiocin 1, isolated from Streptomyces antibioticus, is described. Thus, a concise synthesis of (S)-2-methylcysteine hydrochloride 11 is first developed based on a modification of Seebach's ''self-reproduction of chirality'' protocol using the thiazolidine intermediate 8 derived from (S)-cysteine and pivaldehyde as a key intermediate. When a solution of (S)-2-methylcysteine hydrochloride is heated with 2-cyano-3-hydroxypyridine in the presence of triethylamine, (S)-desferrithiocin is produced in 97% yield. In a similar manner, use of (R)-2-methylcysteine in a cyclocondensation with 2-cyano-3-hydroxypyridine led to (R)-desferrithiocin, in a similar yield.

表征谱图