(alphaR,betaS)-beta-(苯甲酰基氨基)-alpha-(1-乙氧基乙氧基)苯丙酸 | 216094-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (alphaR,betaS)-beta-(苯甲酰基氨基)-alpha-(1-乙氧基乙氧基)苯丙酸
• 中文别名: (2R,3S)-N-苯甲酰基-3-苯异丝胺酸乙酯；(2R,3S)-N-苯甲酰基-3-苯基异丝胺酸乙酯
• 英文名称: (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenylisoserine
• 英文别名: (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine；(2R,3S)-N-benzoyl-0-(1-ethoxyethyl)-3-phenylisoserine；2R,3S-N-benzoyl-O-(1-ethoxyethyl)-3-phenylisoserine；(2R,3S)-3-benzamido-2-(1-ethoxyethoxy)-3-phenylpropanoic acid
• CAS: 216094-54-1
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: OKSZFAMAFLHYNJ-CXRLMVSZSA-N

物化性质

• 沸点：
  578.6±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  [(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 、 (alphaR,betaS)-beta-(苯甲酰基氨基)-alpha-(1-乙氧基乙氧基)苯丙酸 生成 [(1R,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  DENIS, JEAN-NOEL;GREENE, ANDREW-ELLIOT;GUENARD, DANIEL;GUERITTE-VOEGELEIN+

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-benzamido-2-(1-ethoxyethoxy)-3-phenylpropanoate 生成 (alphaR,betaS)-beta-(苯甲酰基氨基)-alpha-(1-乙氧基乙氧基)苯丙酸
  参考文献：
  名称：

  DENIS, JEAN-NOEL;GREENE, ANDREW-ELLIOT;GUENARD, DANIEL;GUERITTE-VOEGELEIN+

  摘要：

  DOI：

文献信息

• Method for preparation of taxol using an oxazinone
  申请人：Florida State University

  公开号：US05015744A1

  公开（公告）日：1991-05-14

  Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, ethoxyethyl, 2,2,2-trichloroethoxymethyl or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent under effective conditions to cause the oxazinone to react with the alcohol to form a .beta.-amido ester which is suitable for use as an intermediate in the synthesis of taxol.

  制备紫杉醇中间体的过程包括将醇与具有以下结构式的噁唑酮接触：##STR1## 其中R.sub.1为芳基、取代芳基、烷基、烯基或炔基；R.sub.2为氢、乙氧基乙基、2,2,2-三氯乙氧甲基或其他羟基保护基；R.sub.3为芳基、取代芳基、烷基、烯基或炔基；在存在足够量的活化剂的情况下，在有效条件下进行醇和噁唑酮的接触，使噁唑酮与醇发生反应形成适用于用作紫杉醇合成中间体的β-酰胺酯。
• Synthesis of taxol, analogs and intermediates with variable A-nng side chains
  申请人：BRYN MAWR COLLEGE

  公开号：EP1260507A1

  公开（公告）日：2002-11-27

  An efficient protocol for the synthesis of taxol, taxol analogs, and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, calphalomanninne and various analogs, including photoaffinity labeling candidates.

  本文介绍了一种有效的紫杉醇、紫杉醇类似物及其中间体的合成协议。该过程包括将紫杉醇A环侧链连接到紫杉醇前体baccatin III上，以及用具有可变A环侧链结构的化合物合成紫杉醇和紫杉醇类似物。通过快速高效的酯化反应，将O保护的异丝氨酸和3-苯基异丝氨酸酸与N-苄氧羰基基团连接到7-O保护的baccatin III的C-13羟基上，然后进行去保护-酰化序列，制备紫杉醇、卡法洛曼宁和各种类似物，包括光亲和标记候选物。
• Chiral catalysts and catalytic epoxidation catalyzed thereby
  申请人：Research Corporation Technologies, Inc.

  公开号：US05637739A1

  公开（公告）日：1997-06-10

  Methods of using chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed. In accordance with one aspect of the invention, the catalyst used is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.

  本发明公开了使用手性催化剂对原构手性烯烃进行对映选择性环氧化和对映选择性氧化原构手性硫化物的方法。根据本发明的一个方面，使用的催化剂是具有以下一般结构的Salen衍生物：##STR1## 根据本发明的另一个方面，公开了使用手性催化剂制备环氧色酮的方法。根据该方法，在所需的条件和时间下，将色酮衍生物、氧原子源和手性催化剂反应以使色酮衍生物环氧化。根据本发明的另一个方面，公开了对顺式-肉桂酸衍生物进行对映选择性环氧化以制备紫杉醇或其类似物的方法。根据另一个方面，公开了使用本发明的催化剂进行过氧化氢的不均化方法。
• Process for the preparation of paclitaxel
  申请人：——

  公开号：US20040049060A1

  公开（公告）日：2004-03-11

  A process for the preparation of paclitaxel starting from 10-deacetylbaccatine III.

  从10-脱乙酰基紫杉醇III开始制备紫杉醇的过程。
• Asymmetric synthesis of taxol side chain
  申请人：Bristol-Myers Squibb Company

  公开号：EP0525589A1

  公开（公告）日：1993-02-03

  The present invention relates to a process for the preparation of (3R, 4S)-3-hydroxy-4-phenyl-2-azetidinone derivatives which are useful intermediates in the synthesis of taxol from baccatin III, and to compounds of formula (III) which are produced in said process: wherein Ar is phenyl; R1 is hydrogen, an acyl radical of a carboxylic acid, or a carbonic acid ester radical; R2 is hydrogen or a carboxy protecting group; and R3 is hydrogen or a hydroxy protecting group.

  本发明涉及一种制备(3R, 4S)-3-羟基-4-苯基-2-氮杂环丁酮衍生物的工艺，该衍生物是由巴卡丁 III 合成紫杉醇的有用中间体，本发明还涉及在上述工艺中制备的式 (III) 化合物： 其中 Ar 是苯基；R1 是氢、羧酸酰基或碳酸酯基；R2 是氢或羧基保护基；R3 是氢或羟基保护基。