(2S*,3R*)-methyl 3-hydroxy-2-(((p-nitrophenyl)sulfonyl)oxy)butanoate | 132486-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S*,3R*)-methyl 3-hydroxy-2-(((p-nitrophenyl)sulfonyl)oxy)butanoate
• 英文别名: methyl 2-<(p-nitrobenzenesulfonyl)oxy>-3-hydroxybutanoate
• CAS: 132486-48-7
• 化学式: C₁₁H₁₃NO₈S
• 分子量: 319.292
• InChiKey: GWNHLNLXBBSNHO-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  133.04
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S*,3R*)-methyl 3-hydroxy-2-(((p-nitrophenyl)sulfonyl)oxy)butanoate 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 以49%的产率得到methyl 2-azido-3-hydroxybutanoate
  参考文献：
  名称：

  Selective transformations of threo-2,3-dihydroxy esters

  摘要：

  Two highly regio- and stereoselective transformation of threo-2,3-dihydroxy esters have been developed. In the first reaction, the alpha-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the alpha-tosylates and alpha-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield. The alpha-nosylates are also suitable electrophiles for azides, giving access to erythro-alpha-azido-beta-hydroxy esters. The second reaction involves conversion of the diol esters to acetoxy bromo esters. The beta-substituent plays a key role in determining the regiochemistry since cases with beta-alkyl substituents afford beta-acetoxy-alpha-bromo esters exclusively, whereas a beta-phenyl substituent directs formation of the alpha-acetoxy-beta-bromo ester. The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.

  DOI：

  10.1021/jo00008a051
• 作为产物：
  描述：

  Methyl 2-<<(p-nitrophenyl)sulfonyl>oxy>acetoacetate 在 sodium tetrahydroborate 作用下， 生成 ethyl (2S,3R)-3-hydroxy-2-(((4-nitrophenyl)sulfonyl)oxy)-3-phenylpropanoate 、 (2S*,3R*)-methyl 3-hydroxy-2-(((p-nitrophenyl)sulfonyl)oxy)butanoate
  参考文献：
  名称：

  使用芳烃磺酰氧基的合成转化，首先作为亲电试剂，然后作为离去基团

  摘要：

  DOI：

  10.1016/s0040-4020(01)86369-9

文献信息

• Synthesis and reactions of 3-hydroxy-2-nosyloxy esters produced by the stereoselective reduction of 2-nosyloxy-3-keto esters
  作者：Robert V. Hoffman、Hwa Ok Kim

  DOI：10.1021/jo00024a013

  日期：1991.11

  The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters. The reduction is stereoselective for the syn isomer. The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters. The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters. As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.