methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate | 145438-00-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate
• 英文别名: methyl (2R,3S)-3-chloro-2-hydroxy-3-phenylpropanoate
• CAS: 145438-00-2；145438-01-3
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: OZWSWCDGHNEYLG-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate 在 palladium on activated charcoal sodium azide 、 lipase Meito SL 、 氢气 、 potassium carbonate 、 氯化铵 作用下， 以 甲醇 、 异丙醚 、 水 、 丙酮 为溶剂， -20.0~35.0 ℃ 、101.33 kPa 条件下， 反应 143.0h， 生成 甲基(2S,3S)-N-boc-3-苯基异丝氨酸盐酸
  参考文献：
  名称：

  紫杉醇（Taxol）和多西紫杉醇（Taxotere）C-13侧链的化学酶法合成

  摘要：

  用各种还原剂还原3-氯-2-氧代-3-苯基丙酸甲酯，得到顺式和反式-3-氯-2-羟基-3-苯基丙酸酯3，它们经过有效的脂肪酶催化分解。随后将所有四个非对映异构体转化为N-苯甲酰基-（2 R，3 S）-3-苯基异丝氨酸甲酯，紫杉醇（Taxol）的C-13侧链类似物。

  DOI：

  10.1016/s0957-4166(00)00418-3
• 作为产物：
  描述：

  methyl trans-3-phenylglycidate 在 盐酸 、 氢溴酸 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Selektive Addition von gasf�rmigem Chlorwasserstoff an kristalline Epoxide und Steroid-Epoxide

  摘要：

  Solid epoxides add gaseous HCl or HBr regioselectively and without melting, if the melting points are sufficiently high. Such additions proceed diastereoselectively with chiral epoxides. These gas/solid reactions are compared to similar transformations in solution. One observes interesting reaction sequences in the conversions of steroidal epoxides. Thus, the opening of the epoxide ring may be followed by cationic rearrangements, or it occurs elimination of water, if it creates conjugation to a carbonyl group.

  DOI：

  10.1002/prac.19923340503

文献信息

• Synthesis of oxazolidines using DMSO/P4O10 as a formaldehyde equivalent
  作者：Jianmei Wang、Fernande D. Rochon、Yan Yang、Ling Hua、Margaret M. Kayser

  DOI：10.1016/j.tetasy.2007.04.017

  日期：2007.5

  Compounds containing a substituted oxazolidine ring were prepared in excellent yields in two steps from cis or trans 3-phenylglycidate. When an electron donating amine was used in the nucleophilic opening of an epoxide, treatment of the resulting beta-amino-alpha-hydroxy ester with DMSO/P4O10 led to the formation of cis or trans oxazolidines. This simple and practical procedure was readily adapted to the synthesis of enantiopure oxazolidines, using DMSO/P4O10 because of the availability of the enantiopure halohydrins from enzymatic reduction of the beta-chloro-alpha-ketoester. (C) 2007 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)
  作者：Hiromi Hamamoto、Vakhid A Mamedov、Makiko Kitamoto、Nobuyuki Hayashi、Sadao Tsuboi

  DOI：10.1016/s0957-4166(00)00418-3

  日期：2000.11

  anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).

  用各种还原剂还原3-氯-2-氧代-3-苯基丙酸甲酯，得到顺式和反式-3-氯-2-羟基-3-苯基丙酸酯3，它们经过有效的脂肪酶催化分解。随后将所有四个非对映异构体转化为N-苯甲酰基-（2 R，3 S）-3-苯基异丝氨酸甲酯，紫杉醇（Taxol）的C-13侧链类似物。
• Selektive Addition von gasf�rmigem Chlorwasserstoff an kristalline Epoxide und Steroid-Epoxide
  作者：Gerd Kaupp、Anke Ulrich、Gerhard Sauer

  DOI：10.1002/prac.19923340503

  日期：——

  Solid epoxides add gaseous HCl or HBr regioselectively and without melting, if the melting points are sufficiently high. Such additions proceed diastereoselectively with chiral epoxides. These gas/solid reactions are compared to similar transformations in solution. One observes interesting reaction sequences in the conversions of steroidal epoxides. Thus, the opening of the epoxide ring may be followed by cationic rearrangements, or it occurs elimination of water, if it creates conjugation to a carbonyl group.