(2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester

• 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: (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester
• 英文别名: DL-threo-Phe(β-OH)OEt；(2RS,3SR)-2-Amino-3-hydroxy-3-phenyl-propionsaeure-aethylester；ethyl (2R,3S)-2-amino-3-hydroxy-3-phenylpropanoate
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: RCUYHYDTFXMONZ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester 在 硫酸 、 硝酸 作用下， 生成 (2RS,3SR)-3-acetoxy-2-acetylamino-3-(4-nitro-phenyl)-propionic acid ethyl ester
  参考文献：
  名称：

  Feitelson et al., Journal of Pharmacy and Pharmacology, 1951, vol. 3, p. 149,155

  摘要：

  DOI：
• 作为产物：
  描述：

  N-acetyl-erythro-DL-β-phenylserine ethyl ester 在 盐酸 、 氯化亚砜 作用下， 生成 (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester
  参考文献：
  名称：

  β-Phenylserine

  摘要：

  DOI：

  10.1021/ja01141a070

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。
• Studies on Antibiotics and Related Substances. III. Oxazolidines Derived from Some α-Hydroxy Schiff Bases and a Synthesis of DL-<i>threo</i>-1-<i>p</i>-Nitrophenyl-2-amino-1,3-propanediol
  作者：Tetsuo Suami、Sumio Umezawa

  DOI：10.1246/bcsj.29.979

  日期：1956.9

  and p-nitrobenzaldehyde were prepared and acetylated to give corresponding oxazolidine derivatives, which failed to hydrolyze under Kunz’s conditions. Infrared and ultraviolet absorption spectra of some of these compounds were observed. Acetylated derivatives failed to show the characteristic absorption of (Remark: Graphics omitted.) bond in the 1660–1610 cm−1 region. 4) DL-Chloramphenicol was synthesiz

  1) 用雷尼镍催化剂还原 Erlenmeyer β-苯基丝氨酸乙酯，得到 DL-threo-1-phenyl-2-benzylideneamino-1, 3-propanediol（一种席夫碱）作为主要产物。通过其红外和紫外吸收光谱证明了该结构。2) 发现 DL-threo-1-phenyl-2-benzylideneamino-1, 3-propanediol 在用乙酸酐乙酰化后得到 DL-threo-N-acetyl-2-phenyl-4-(α-hydroxybenzyl) oxazolidine。3) DL-threo-1-phenyl-2-amino-1, 3-propanediol 和 DL-threo-1-p-nitrophenyl-2-amino-1, 3-propanediol 与苯甲醛的缩合产物，o-, m - 和对硝基苯甲醛被制备并乙酰化得到相应的恶唑烷衍生物，其在昆茨
• Sul cloroamfenicolo (cloromicetina). Sintesi di isomeri ed analoghi del cloroamfenicolo. Nota II
  作者：J. Büchi、S. Contini、H. Hurni、R. Lieberherr

  DOI：10.1002/hlca.19510340614

  日期：——

  No abstract is available for this article.

  本文没有摘要。
• Addition of Azomethine Ylides to Aldehydes: Mechanistic Dichotomy of Differentially Substituted α-Imino Esters
  作者：Brinton Seashore-Ludlow、Staffan Torssell、Peter Somfai

  DOI：10.1002/ejoc.201000377

  日期：——

  of azomethine ylides and aldehydes is explored, as hydrolysis of the resulting oxazolidine product gives facile access to valuable syn-β-aryl-β-hydroxy-α-amino esters. The use of using benzaldehyde-derived imines as the ylide precursor results in 1,3-dipolar cycloaddition with high conversions but low diastereoselectivity. In contrast, the employment of benzophenone-derived imines as the ylide precursor

  探索了偶氮甲碱叶立德和醛的正式 1,3-偶极环加成反应，因为所得恶唑烷产物的水解可以轻松获得有价值的顺-β-芳基-β-羟基-α-氨基酯。使用苯甲醛衍生的亚胺作为叶立德前体导致 1,3-偶极环加成反应具有高转化率但非对映选择性低。相比之下，使用二苯甲酮衍生的亚胺作为叶立德前体会导致羟醛反应，从而产生具有高非对映选择性的中间体恶唑烷，并且需要弱酸催化剂来实现更高的转化率。
• Studies on Antibiotics and Related Substances. IV. Synthesis of DL-threo-β-Cyclohexylserine and DL-threo-2-Dichloroacetamido-1-cyclohexylpropane-1,3-diol
  作者：Sumio Umezawa、Yoshihisa Oguma

  DOI：10.1246/bcsj.29.987

  日期：1956.9

  When the N-acetyl ethyl ester of Erlenmeyer’s phenylserine was reduced with hydrogen over Raney nickel catalyst, ethyl DL-threo-N-acetyl-β-cyclohexylserinate was obtained in crude yields as high as 86.8 %. Subsequent hydrolysis with dilute hydrochloric acid afforded DL-threo-β-cyclohexylserine, which gave hexahydrobenzaldehyde by periodate oxidation. (2) Raney nickel reduction of ethyl DL-threo-β-cyclohexyl-serinate

  (1) Erlenmeyer苯丝氨酸的N-乙酰乙酯在阮内镍催化剂上用氢气还原，得到DL-苏式-N-乙酰-β-环己基丝氨酸乙酯，粗收率高达86.8%。随后用稀盐酸水解得到 DL-苏-β-环己基丝氨酸，通过高碘酸盐氧化得到六氢苯甲醛。(2) DL-threo-β-环己基丝氨酸乙酯的阮内镍还原得到DL-threo-2-amino-1-cyclohexylpropane-1, 3-diol。氨基醇被转化为 DL-threo-2-dichloroacetamido-1-cyclohexylpropane-1,3-diol，一种氯霉素类似物。