(4S,5R)-5-methoxycarbonyl-4-phenyl-2-trichloromethyl-1,3-oxazolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5R)-5-methoxycarbonyl-4-phenyl-2-trichloromethyl-1,3-oxazolidine
• 英文别名: methyl (4S,5R)-4-phenyl-2-(trichloromethyl)-1,3-oxazolidine-5-carboxylate
• 化学式: C₁₂H₁₂Cl₃NO₃
• 分子量: 324.591
• InChiKey: YWIMYRQHWIPVFP-VUHGHZMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-methoxycarbonyl-4-phenyl-2-trichloromethyl-1,3-oxazolidine 在 4-二甲氨基吡啶 、 lithium hydroxide 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 34.0h， 生成 多西他赛
  参考文献：
  名称：

  Expeditious semisynthesis of docetaxel using 2-trichloromethyl-1,3-oxazolidine as side-chain protection

  摘要：

  Chloral reacts with phenylisoserine and N-Boc-phenylisoserine methyl esters to give N-unprotected 2-trichloromethyl-1,3-oxazolidines 4+4'. The corresponding oxazolidinecarboxylic acids 5+5' were esterified by 10-desacetyl-7,10-diTroc-baccatin III. Concomitant deprotection of the Tree and 2-trichloromethylmethylene groups was achieved under reducing conditions (Zn, AcOH). The recovered product 7 was acylated with di-tert-butyldicarbonate to give docetaxel 1.

  DOI：

  10.1016/s0040-4039(00)76828-6
• 作为产物：
  描述：

  (2R,3S)-N-叔丁氧羰基-3-苯基异丝氨酸甲酯 、 三氯乙醛 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以91%的产率得到(4S,5R)-5-methoxycarbonyl-4-phenyl-2-trichloromethyl-1,3-oxazolidine
  参考文献：
  名称：

  Expeditious semisynthesis of docetaxel using 2-trichloromethyl-1,3-oxazolidine as side-chain protection

  摘要：

  Chloral reacts with phenylisoserine and N-Boc-phenylisoserine methyl esters to give N-unprotected 2-trichloromethyl-1,3-oxazolidines 4+4'. The corresponding oxazolidinecarboxylic acids 5+5' were esterified by 10-desacetyl-7,10-diTroc-baccatin III. Concomitant deprotection of the Tree and 2-trichloromethylmethylene groups was achieved under reducing conditions (Zn, AcOH). The recovered product 7 was acylated with di-tert-butyldicarbonate to give docetaxel 1.

  DOI：

  10.1016/s0040-4039(00)76828-6

文献信息

• Process for the preparation of taxane derivatives
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05621121A1

  公开（公告）日：1997-04-15

  This invention relates to a method of preparing taxane derivatives of formula (I) by esterification of protected baccatin III or 10-deacetylbaccatin III by means of an acid of formula (VII), elimination of protection groupings and acylation of the amine function of the side chain. The products of formula (I) have remarkable antitumor and antileukemia properties. In formulae (I) and (VII): Ar stands for aryl, R is hydrogen or acetyl, R.sub.1 is a benzoyl radical or an R.sub.2 --O--CO-- radical in which R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, phenyl or heterocyclyl, R.sub.3 is a trihalomethyl radical or phenyl substituted by a trihalomethyl radical, R.sub.4 is a hydrogen atom or is the same as R.sub.1. ##STR1##

  本发明涉及一种通过使用公式（VII）的酸酯化保护的baccatin III或10-去乙酰基baccatin III，去除保护基团并酰化侧链的胺基功能来制备公式（I）的紫杉醇衍生物的方法。公式（I）的产物具有显著的抗肿瘤和抗白血病性质。在公式（I）和（VII）中：Ar代表芳基，R为氢或乙酰基，R.sub.1是苯甲酰基基团或R.sub.2-O-CO-基团，其中R.sub.2是烷基，烯基，炔基，环烷基，环烯基，双环烷基，苯基或杂环基，R.sub.3是三卤甲基基团或经三卤甲基基团取代的苯基，R.sub.4是氢原子或与R.sub.1相同。 ##STR1##
• US5621121A
  申请人：——

  公开号：US5621121A

  公开（公告）日：1997-04-15
• US5726318A
  申请人：——

  公开号：US5726318A

  公开（公告）日：1998-03-10
• US5861515A
  申请人：——

  公开号：US5861515A

  公开（公告）日：1999-01-19
• Expeditious semisynthesis of docetaxel using 2-trichloromethyl-1,3-oxazolidine as side-chain protection
  作者：Eric Didier、Elie Fouque、Alain Commerçon

  DOI：10.1016/s0040-4039(00)76828-6

  日期：1994.5

  Chloral reacts with phenylisoserine and N-Boc-phenylisoserine methyl esters to give N-unprotected 2-trichloromethyl-1,3-oxazolidines 4+4'. The corresponding oxazolidinecarboxylic acids 5+5' were esterified by 10-desacetyl-7,10-diTroc-baccatin III. Concomitant deprotection of the Tree and 2-trichloromethylmethylene groups was achieved under reducing conditions (Zn, AcOH). The recovered product 7 was acylated with di-tert-butyldicarbonate to give docetaxel 1.