methyl (2R,3S)-2-hydroxy-3-[(S)-1-phenyl]ethylamino-3-(4-fluorophenyl)propionate | 154306-84-0

• 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)-2-hydroxy-3-[(S)-1-phenyl]ethylamino-3-(4-fluorophenyl)propionate
• 英文别名: methyl (2R,3S)-3-(4-fluorophenyl)-2-hydroxy-3-[[(1S)-1-phenylethyl]amino]propanoate
• CAS: 154306-84-0
• 化学式: C₁₈H₂₀FNO₃
• 分子量: 317.36
• InChiKey: HKTWHLAFWIFGHZ-AFAVFJNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2-hydroxy-3-[(S)-1-phenyl]ethylamino-3-(4-fluorophenyl)propionate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 65.0 ℃ 、2.38 MPa 条件下， 反应 4.0h， 生成 methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate
  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：

  在 盐酸 、 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 methyl (2R,3S)-2-hydroxy-3-[(S)-1-phenyl]ethylamino-3-(4-fluorophenyl)propionate
  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

• Process for the preparation of .beta.-phenylisoserine and .beta.-lactam
  申请人：Rhone-Poulence Rorer S.A.

  公开号：US05939561A1

  公开（公告）日：1999-08-17

  The present invention relates to new process for the preparation of .beta.-phenylisoserine and its analogues of general formula: ##STR1## which are particularly useful for preparing taxane derivatives which have remarkable antitumour and antileukaemic activities.

  本发明涉及一种新的制备β-苯基异丝氨酸及其类似物的方法，其一般化学式如下：##STR1## 这些化合物特别适用于制备具有显著抗肿瘤和抗白血病活性的紫杉醇衍生物。
• Process for the preparation of .beta.-phenylisoserine and its analogues
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05608102A1

  公开（公告）日：1997-03-04

  This invention relates to a method for preparing .beta.-phenylisoserine and analogues thereof having general formula (I) ##STR1## from an aromatic aldehyde and an .alpha.-methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of general formula (I) (R.dbd.H) may be used to prepare taxane derivatives having remarkable antitumoral and antileukaemic activity.

  这项发明涉及一种制备β-苯基异丝氨酸及其类似物的方法，其通式为(I)。从芳香醛和α-甲基芳基胺-S，以及本文所述的通式(II)的内酰胺中制备。通式(I)中的酸(R=H)可用于制备具有显著抗肿瘤和抗白血病活性的紫杉醇衍生物。
• 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).