methyl (4S,5R)-4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide | 1300732-33-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: methyl (4S,5R)-4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide
• CAS: 1300732-33-5
• 化学式: C₆H₁₁NO₅S
• 分子量: 209.223
• InChiKey: CXDQUSVGAROKSS-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.11
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (4S,5R)-4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide 在 benzyltriethylammonium tetrathiomolybdate 、 柠檬酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以79%的产率得到methyl N-[(2S,3S)-3-sulfanylbutan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of amino thiols and isocysteines via regioselective ring opening of sulfamidates with tetrathiomolybdate

  摘要：

  Herein we present a simple and highly efficient method for the synthesis of beta and gamma-amino thiols via regioselective ring opening of sulfamidates with tetrathiomolybdate 1. The generality of this methodology has been shown by synthesizing carbohydrate derived beta-amino thiol. The scope and versatility of this methodology has been demonstrated by synthesizing biologically important unnatural amino acids like isocysteines in optically pure form. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.074
• 作为产物：
  描述：

  伯吉斯试剂 、 (2R,3R)-(-)-2,3-丁二醇 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (4S,5R)-4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide
  参考文献：
  名称：

  Synthesis of amino thiols and isocysteines via regioselective ring opening of sulfamidates with tetrathiomolybdate

  摘要：

  Herein we present a simple and highly efficient method for the synthesis of beta and gamma-amino thiols via regioselective ring opening of sulfamidates with tetrathiomolybdate 1. The generality of this methodology has been shown by synthesizing carbohydrate derived beta-amino thiol. The scope and versatility of this methodology has been demonstrated by synthesizing biologically important unnatural amino acids like isocysteines in optically pure form. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.074