(2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester | 130517-92-9

• 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: (2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester
• 英文别名: Owofstzblzmvep-rkdxnwhrsa-；methyl (2R,3R)-2-azido-3-hydroxy-3-phenylpropanoate
• CAS: 130517-92-9
• 化学式: C₁₀H₁₁N₃O₃
• 分子量: 221.216
• InChiKey: OWOFSTZBLZMVEP-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester 在 4-二甲氨基吡啶 、 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 为溶剂， 反应 21.0h， 生成 (2R,3R)-2-(2-cyclopropylacetylamino)-3-hydroxy-3-phenylpropionic 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：

  (2S,3R)-(-)-2,3-二羟基-3-苯基丙酸甲酯 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 (2R,3R)-2-azido-3-phenyl-3-hydroxypropionic 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

文献信息

• Chemo-enzymatic synthesis of all isomeric 3-phenylserines and -isoserines
  作者：H. Hönig、P. Seufer-Wasserthal、H. Weber

  DOI：10.1016/s0040-4020(01)90519-8

  日期：1990.1

  prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps. These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines. The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic

  提供了对映体纯形式的3-苯基丝氨酸和3-苯基异丝氨酸的所有异构体的合成。非对映体纯离析物（苏/赤-2--叠氮基-3-丁酰氧基-3-苯基丙酸酯，苏/赤-3-叠氮--2-丁酰氧基-3-苯基丙酸酯，苏二-2-丁酰基氨基-3-丁酰氧基-由肉桂酸衍生物或通过苯甲醛与合适的烯醇酸酯的醛醇缩合在几个步骤中制备3-苯基丙酸酯，赤型-3-丁酰基氨基-2-丁酰基氧基-3-苯基丙酰胺。用消旋假丝酵母和荧光假单胞菌的脂肪酶分离了这些外消旋体（P）并将获得的产物氢化成3-苯基丝氨酸和-异丝氨酸。研究了酰基对赤型-3-叠氮基-2-酰氧基-3-苯基丙酸酯的酶促拆分的影响。
• Enhancing Activity and Controlling Stereoselectivity in a Designed PLP-Dependent Aldolase
  作者：Miguel D. Toscano、Manuel M. Müller、Donald Hilvert

  DOI：10.1002/anie.200700710

  日期：2007.6.11
• Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines
  作者：Christoffer Bengtsson、Hanna Nelander、Fredrik Almqvist

  DOI：10.1002/chem.201301120

  日期：2013.7.22

  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.