(2S,3R)-(-)-methyl 3-hydroxy-2-(((p-nitrophenyl)sulfonyl)oxy)3-phenylpropionate | 132377-67-4

• 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)3-phenylpropionate
• 英文别名: (2S,3R)-3-hydroxy-2-(4-nitrobenzenesulfonyloxy)-3-phenylpropionic acid methyl ester；methyl (2S,3R)-3-hydroxy-2-(4-nitrophenyl)sulfonyloxy-3-phenylpropanoate
• CAS: 132377-67-4
• 化学式: C₁₆H₁₅NO₈S
• 分子量: 381.363
• InChiKey: DXMPFDYJKZTYSL-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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)3-phenylpropionate 在 4-二甲氨基吡啶 、 sodium azide 、 tin(II) chloride dihdyrate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 (2R,3R)-3-hydroxy-3-phenyl-2-(2-thiophen-2-ylacetylamino)propionic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines

  摘要：

  AbstractΔ2‐Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5‐trisubstituted Δ2‐thiazolines. These Δ2‐thiazolines were synthesized from readily accessible/commercially available α,β‐unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.

  DOI：

  10.1002/chem.201301120
• 作为产物：
  描述：

  Methyl cinnamate 在 甲基磺酰胺 、 AD-mix-β 、 水 、 三乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 19.0h， 生成 (2S,3R)-(-)-methyl 3-hydroxy-2-(((p-nitrophenyl)sulfonyl)oxy)3-phenylpropionate
  参考文献：
  名称：

  Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines

  摘要：

  AbstractΔ2‐Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5‐trisubstituted Δ2‐thiazolines. These Δ2‐thiazolines were synthesized from readily accessible/commercially available α,β‐unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.

  DOI：

  10.1002/chem.201301120

文献信息

• Selective transformations of threo-2,3-dihydroxy esters
  作者：Paul R. Fleming、K. Barry Sharpless

  DOI：10.1021/jo00008a051

  日期：1991.4

  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.
• FLEMING, PAUL R.;SHARPLESS, K. BARRY, J. ORG. CHEM., 56,(1991) N, C. 2869-2875
  作者：FLEMING, PAUL R.、SHARPLESS, K. BARRY

  DOI：——

  日期：——