methyl (2R,3S)-3-amino-3-[4-(dimethylamino)phenyl]-2-hydroxypropanoate | 157157-65-8

• 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: methyl (2R,3S)-3-amino-3-[4-(dimethylamino)phenyl]-2-hydroxypropanoate
• CAS: 157157-65-8
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: RKJJXBWYJVYIPC-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-amino-3-[4-(dimethylamino)phenyl]-2-hydroxypropanoate 在 4-甲基苯磺酸吡啶 、 sodium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.0h， 生成 (4S,5R)-4-(4-Dimethylamino-phenyl)-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester
  参考文献：
  名称：

  A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs

  摘要：

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).

  DOI：

  10.1016/s0040-4039(00)61724-0
• 作为产物：
  描述：

  (3R,4S)-3-hydroxy-4-(4-dimethylaminophenyl)-1-[(S)-1-phenyl]ethyl-2-azetidinone 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 40.0~65.0 ℃ 、2.38 MPa 条件下， 反应 6.5h， 生成 methyl (2R,3S)-3-amino-3-[4-(dimethylamino)phenyl]-2-hydroxypropanoate
  参考文献：
  名称：

  A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs

  摘要：

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).

  DOI：

  10.1016/s0040-4039(00)61724-0

文献信息

• A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs
  作者：Jean Dominique Bourzat、Alain Commerçon

  DOI：10.1016/s0040-4039(00)61724-0

  日期：1993.9

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).