(2S,4S,1R,2R,3R)-2-(1,2,3,4-Tetrahydroxybutyl)-5,5-dimethyl-4-thiazolidincarbonsaeure

• 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,1R,2R,3R)-2-(1,2,3,4-Tetrahydroxybutyl)-5,5-dimethyl-4-thiazolidincarbonsaeure
• 英文别名: (2S,4S)-5,5-dimethyl-2-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-1,3-thiazolidine-4-carboxylic acid
• 化学式: C₁₀H₁₉NO₆S
• 分子量: 281.33
• InChiKey: GFMBLCOHHQMUAY-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,4S,1R,2R,3R)-2-(1,2,3,4-Tetrahydroxybutyl)-5,5-dimethyl-4-thiazolidincarbonsaeure 在 甲烷磺酸 作用下， 反应 20.0h， 以23%的产率得到(2S,4S,1S,2R,3R)-3-Acetyl-2-(1,2,3,4-tetraacetoxybutyl)-5,5-dimethyl-4-thiazolidincarbonsaeure
  参考文献：
  名称：

  Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbons�uren. Chiralit�tstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen

  摘要：

  5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3 + 2]-cycloaddition reactions via mesoionic oxazolone (''munchnone'') intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through H-1- and CD-spectra and the molecular structure of (3S)-3da has been determined by X-ray crystallography.

  DOI：

  10.1007/bf00818164

文献信息

• Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbons�uren. Chiralit�tstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen
  作者：Z. Gy�rgyde�k、L. Szil�gyi、J. Kajt�r、G. Argay、A. K�lm�n

  DOI：10.1007/bf00818164

  日期：1994.2

  5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3 + 2]-cycloaddition reactions via mesoionic oxazolone (''munchnone'') intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through H-1- and CD-spectra and the molecular structure of (3S)-3da has been determined by X-ray crystallography.