(2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid | 155396-65-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid
• 英文别名: (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropionic acid；(2R,3S)-2-benzyloxy-3-t-butoxycarbonylamino-3-phenylpropionic acid；(2R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenyl-2-phenylmethoxypropanoic acid
• CAS: 155396-65-9
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: RPYBPNSJLCUOBD-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid 在 钯 4-二甲氨基吡啶 、 氢气 、 铜 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 反应 26.58h， 生成 多西他赛
  参考文献：
  名称：

  Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain

  摘要：

  A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (greater-than-or-equal-to 99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.

  DOI：

  10.1021/jo00085a004
• 作为产物：
  描述：

  benzaldehyde N-boc imine 在 lithium hydroxide 、 双氧水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.25h， 生成 (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid
  参考文献：
  名称：

  Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain

  摘要：

  A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (greater-than-or-equal-to 99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.

  DOI：

  10.1021/jo00085a004

文献信息

• [EN] PROCESS FOR PREPARING DOCETAXEL AND ITS HYDRATE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DOCÉTAXEL ET DE SON HYDRATE
  申请人：SHILPA MEDICARE LTD

  公开号：WO2012131698A1

  公开（公告）日：2012-10-04

  Disclosed is a process of preparation of (2R,3S)-N-carboxy-3-phenylisoserine, N-tert-butyl ester, 13-ester with 5(P)-20-epoxy-l,2(a), 4,7(P), 10(β), 13(a)-hexa hydroxyl tax-l l-en-9-one 4-acetate 2-benzoate (docetaxel) and its trihydrate (I).

  披露了一种制备(2R,3S)-N-羧基-3-苯基异丝氨酸N-叔丁基酯，13-酯与5(P)-20-环氧-1,2(a),4,7(P),10(β),13(a)-六羟基紫杉醇-11-烯-9-酮-4-醋酸酯-2-苯甲酸酯（多西紫杉醇）及其三水合物（I）的过程。
• [EN] PREPARATION OF ß-PHENYL-ISOSERINE DERIVATIVES<br/>[FR] PRÉPARATION DE DÉRIVÉS DE ?-PHÉNYL-ISOSÉRINE
  申请人：ORGANOCLICK AKTIEBOLAG

  公开号：WO2010024762A1

  公开（公告）日：2010-03-04

  A process for stereoselective synthesis of a β-phenylisoserine comprises reacting a carbonyl imine R-C=N-CO-OR1 with a protected α- oxyaldehyde X1O-CH2CHO in the presence of a chiral amine catalyst and oxidizing aldehyde so obtained.

  一种立体选择性合成β-苯基异丝氨酸的方法，包括在手性胺催化剂的存在下，将羰基亚胺R-C=N-CO-OR1与保护的α-氧代醛X1O-CH2CHO反应，并氧化获得的醛。
• Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready α-hydroxy-β-amino acids
  作者：Pawel Dziedzic、Jan Vesely、Armando Córdova

  DOI：10.1016/j.tetlet.2008.09.038

  日期：2008.11

  A highly enantioselective catalytic route to protected β-amino-α-hydroxy acids, such as the side chain of Taxotere, is presented. The organocatalytic asymmetric reactions between unmodified protected α-oxyaldehydes and N-Boc-protected aryl imines give the corresponding compound with up to >19:1 dr and 99–99% ee.

  提出了对被保护的β-氨基-α-羟基酸（如Taxotere的侧链）的高度对映选择性催化路线。未经修饰的受保护的α-氧醛与N -Boc保护的芳基亚胺之间的有机催化不对称反应可得到相应的化合物，其dr> 19：1，ee可达99-99％。
• [EN] PROCESS FOR PREPARING (2R, 3S) 2-BENZYLOXY-3-TERT-BUTOXY CARBONYL AMINO-3-PHENYL PROPIONIC ACID<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDE (2R, 3S)-2-BENZYLOXY-3-TERT-BUTOXY-CARBONYL AMINO-3-PHÉNYL PROPIONIQUE
  申请人：SHILPA MEDICARE LTD

  公开号：WO2012117417A1

  公开（公告）日：2012-09-07

  A method for preparing(2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropionic acid of formula (I) is provided, and a method for purifying and isolating the compound is also provided. The method uses inexpensive, non-hazardous and easily available reagents and results in better yields and purity.

  提供了一种制备（2R，3S）-2-苄氧基-3-叔丁氧羰基氨基-3-苯基丙酸（I）的方法，并提供了一种纯化和分离该化合物的方法。该方法使用廉价、无危险性和易得的试剂，产率和纯度更高。
• PROCESS FOR PREPARING DOCETAXEL AND ITS HYDRATE
  申请人：Shrawat Vimal Kumar

  公开号：US20140039209A1

  公开（公告）日：2014-02-06

  The present invention provide process of preparation of (2R,3S)—N-carboxy-3-phenylisoserine, N-tert-butyl ester, 13-ester with 5(β)-20-epoxy-1,2(α),4,7(β),10(β),13(α)-hexa hydroxy tax-11-en-9-one 4-acetate 2-benzoate or docetaxel and its trihydrate (I)