(2R,3R)-ethyl 2-bromo-3-hydroxy-3-phenylpropanoate | 757232-69-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3R)-ethyl 2-bromo-3-hydroxy-3-phenylpropanoate
• 英文别名: (-)-ethyl (2R,3R)-2-bromo-3-hydroxy-3-phenylpropanoate；ethyl rel-(2R,3R)-2-bromo-3-hydroxy-3-phenylpropanoate；ethyl (2R,3R)-2-bromo-3-hydroxy-3-phenylpropanoate
• CAS: 757232-69-2
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: VCVOZQQASPCFJH-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-ethyl 2-bromo-3-hydroxy-3-phenylpropanoate 以90%的产率得到
  参考文献：
  名称：

  HONIG, H.;SEUFER-WASSERTHAL, P.;WEBER, H., TETRAHEDRON, 46,(1990) N1, C. 3841-3850

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (4S,5R)-2,2-dioxo-5-phenyl-1,3,2-dioxathiolane-4-carboxylate 在 硫酸 、 lithium bromide 作用下， 生成 (2R,3R)-ethyl 2-bromo-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  通过环状硫酸盐中间体高效合成手性α，β-环氧酯

  摘要：

  手性α，β环氧酯的有效的合成1从手性2,3- dihydroxyester 2已经研制成功。将酯2转化为相应的环状硫酸盐3，将其在室温下用THF中的LiBr或在丙酮中的Bu 4 NBr打开，以提供2-溴-3-羟基酯4。在甲醇中在低温下用K 2 CO 3处理4，得到的α，β-环氧酯1的总收率极好，且ee与起始二醇相同。

  DOI：

  10.1016/s0040-4039(98)00190-7

文献信息

• Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins
  作者：Naveen Anand、Munish Kapoor、Surrinder Koul、Subhash C. Taneja、Rattan L. Sharma、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2004.08.026

  日期：2004.10

  Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem. were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched (2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein, including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)phenylglycidates. (C) 26 E'lsevier Ltd. All rights reserved.
• SHIN CHUNG-GI; YONEZAWA YASUCHIKA; UNOKI KAZUO; YOSHIMURA YUJI, BULL. CHEM. SOC. JAP., 1979, 52, NO 6, 1657-1660
  作者：SHIN CHUNG-GI、 YONEZAWA YASUCHIKA、 UNOKI KAZUO、 YOSHIMURA YUJI

  DOI：——

  日期：——
• HONIG, H.;SEUFER-WASSERTHAL, P.;WEBER, H., TETRAHEDRON, 46,(1990) N1, C. 3841-3850
  作者：HONIG, H.、SEUFER-WASSERTHAL, P.、WEBER, H.

  DOI：——

  日期：——
• US7060471B2
  申请人：——

  公开号：US7060471B2

  公开（公告）日：2006-06-13
• Efficient synthesis of chiral α,β-epoxyesters via a cyclic sulfate intermediate
  作者：Linli He、Hoe-Sup Byun、Robert Bittman

  DOI：10.1016/s0040-4039(98)00190-7

  日期：1998.4

  An efficient synthesis of chiral α,β-epoxyester 1 from chiral 2,3-dihydroxyester 2 has been developed. Ester 2 is converted to the corresponding cyclic sulfate 3, which is opened with either LiBr in THF or Bu4NBr in acetone at rt to furnish 2-bromo-3-hydroxyester 4. Treatment of 4 with K2CO3 in methanol at low temperature gives α,β-epoxyester 1 in excellent overall yield and in the same ee as in the

  手性α，β环氧酯的有效的合成1从手性2,3- dihydroxyester 2已经研制成功。将酯2转化为相应的环状硫酸盐3，将其在室温下用THF中的LiBr或在丙酮中的Bu 4 NBr打开，以提供2-溴-3-羟基酯4。在甲醇中在低温下用K 2 CO 3处理4，得到的α，β-环氧酯1的总收率极好，且ee与起始二醇相同。

表征谱图