(S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-[4-(2,6-dichloro-benzyloxy)-phenyl]-propionic acid methyl ester | 610314-22-2

• 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: (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-[4-(2,6-dichloro-benzyloxy)-phenyl]-propionic acid methyl ester
• CAS: 610314-22-2
• 化学式: C₂₇H₂₆Cl₃NO₅
• 分子量: 550.866
• InChiKey: ZGEALTQUTMHMQS-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-[4-(2,6-dichloro-benzyloxy)-phenyl]-propionic acid methyl ester 在 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 、 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 乙腈 为溶剂， 生成 (S)-2-[4-(2,6-Dichloro-benzyloxy)-benzyl]-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 、 (R)-2-[4-(2,6-Dichloro-benzyloxy)-benzyl]-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of amino acid-derived β-lactams. Experimental evidence for TADDOL as a memory of chirality enhancer

  摘要：

  In model experiments, concerning the modulation of memory of chirality during the intramolecular alkylation of N-(Pmethoxy)benzyl-N-chloroacetyl-Phe-O'Bu derivative to the corresponding beta-lactam, TADDOL was selected from a panel of different phase-transfer catalysts as the best chiral additive (ee up to 82%). We have demonstrated here that the degree and sign of the cyclization selectivity was virtually independent on TADDOL configuration, providing experimental proof that in this reaction this additive works as a memory of chirality enhancer and not as a real catalyst. The effect of TADDOL is strongly dependent on the starting amino acid derivative, the increase of selectivity being only observed for those with aromatic side chains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.125
• 作为产物：
  描述：

  (S)-O-(2,6-dichlorobenzyl)tyrosine methyl ester hydrochloride 在 sodium tetrahydroborate 、 三乙胺 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-[4-(2,6-dichloro-benzyloxy)-phenyl]-propionic acid methyl ester
  参考文献：
  名称：

  Memory of chirality in the stereoselective synthesis of β-lactams: importance of the starting amino acid derivative

  摘要：

  The enantioselectivity of the base-promoted cyclization of N-alkyl-N-chloroacetyl amino acid derivatives to beta-lactams is dependent on the substituents on the starting material. While Bu-t esters are preferred over Me esters, and N-Bzl-, N-Pmb, N-Nph and N-Mom groups gave similar e.e. values, only amino acid derivatives with branched side-chains at the gamma-position were able to show a good memory of chirality. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00398-7