(2R,3R)-4-benzyloxy-2,3-epoxybutanoic acid methyl ester | 148407-37-8

• 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: (2R,3R)-4-benzyloxy-2,3-epoxybutanoic acid methyl ester
• 英文别名: methyl (2R-cis)-3-(benzyloxymethyl)oxirane carboxylate；methyl (2R,3R)-3-(phenylmethoxymethyl)oxirane-2-carboxylate
• CAS: 148407-37-8
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: QPCLGMIQGMSKON-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-benzyloxy-2,3-epoxybutanoic acid methyl ester 在 palladium on activated charcoal sodium azide 、 Amberlyst 15 、 氢气 、 二异丁基氢化铝 、 对甲苯磺酸 、 sodium bromide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 36.5h， 生成 (4R,5S)-5-benzyloxymethyl-3-N-tert-butoxycarbonyl-4-formyl-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  D-高效立体选择性合成赤-sphingosine和D-来苏-phytosphingosine

  摘要：

  从一个单一的合适的官能化环氧化物起始，D-的高效立体选择性合成赤-sphingosine和D-来苏-phytosphingosine进行说明。该方法允许形式上制备这些类神经鞘结构的所有立体异构体。

  DOI：

  10.1016/j.tet.2006.08.049
• 作为产物：
  描述：

  顺-4-苄氧基-2-丁烯-1-醇 在 Oxone 、 重铬酸吡啶 、 草酰氯 、 碳酸氢钠 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.0h， 生成 (2R,3R)-4-benzyloxy-2,3-epoxybutanoic acid methyl ester
  参考文献：
  名称：

  A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides

  摘要：

  The results obtained in the MgBr2-mediated opening of 2,3-bifunctionalized epoxides are reported. The studies showed that the chelation control of MgBr2 between different functionalities can in some cases be selective. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00492-6

文献信息

• 2,3-epoxy derivatives as anti retrovital chemotherapeutic agents
  申请人：The United States of America as represented by the Secretary of the

  公开号：US05190969A1

  公开（公告）日：1993-03-02

  The present invention is related to compounds, compositions and methods of treating viral infections. Compounds of the present invention have the following general formula: ##STR1## wherein R is selected from --CH.sub.2 OH, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, or COR.sup.5, wherein R.sup.2 is hydrogen or a lower alkyl group, R.sup.3 and R.sup.4 are each independently hydrogen or a lower alkyl group, R.sup.5 is an amino acid residue bound via a terminal nitrogen or peptide having at least two amino acid residues; and wherein R.sup.1 is C.sub.5 -C.sub.13 alkyl, aryl, aralkyl, aralkyl(lower alkyl) ether, or C.sub.5 -C.sub.13 alkyl (lower alkyl)ether.

  本发明涉及化合物、组合物和治疗病毒感染的方法。本发明的化合物具有以下通用式：##STR1## 其中R从--CH.sub.2 OH、--CO.sub.2 R.sup.2、--CONR.sup.3 R.sup.4或COR.sup.5中选择，其中R.sup.2是氢或低级烷基，R.sup.3和R.sup.4各自独立地是氢或低级烷基，R.sup.5是通过末端氮或至少具有两个氨基酸残基的肽结合的氨基酸残基；R.sup.1是C.sub.5-C.sub.13烷基、芳基、芳基烷基、芳基烷基（低级烷基）醚或C.sub.5-C.sub.13烷基（低级烷基）醚。
• 2,3-epoxy alcohols, acids and derivatives as anti retroviral
  申请人：The United States of America as represented by the Department of Health

  公开号：US06153589A1

  公开（公告）日：2000-11-28

  The present invention is related to compounds, compositions and methods of treating viral infections. Compounds of the present invention have the following general formula: ##STR1## wherein R is selected from --CH.sub.2 OH, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, or COR.sup.5, wherein R.sup.2 is hydrogen or a lower alkyl group, R.sup.3 and R.sup.4 are each independently hydrogen or a lower alkyl group, R.sup.5 is an amino acid residue bound via a terminal nitrogen or peptide having at least two amino acid residues; and wherein R.sup.1 is C.sub.5 -C.sub.13 alkyl, aryl, aralkyl, aralkyl(lower alkyl)ether, or C.sub.5 -C.sub.13 alkyl(lower alkyl)ether.

  本发明涉及化合物、组合物和治疗病毒感染的方法。本发明的化合物具有以下一般式：##STR1## 其中，R从--CH.sub.2 OH、--CO.sub.2 R.sup.2、--CONR.sup.3 R.sup.4或COR.sup.5中选择，其中R.sup.2为氢或低碳基，R.sup.3和R.sup.4各自独立地为氢或低碳基，R.sup.5为通过末端氮键合的氨基酸残基或至少具有两个氨基酸残基的肽；其中R.sup.1为C.sub.5-C.sub.13烷基、芳基、芳基烷基、芳基烷基（低碳基）醚或C.sub.5-C.sub.13烷基（低碳基）醚。
• Regiochemical control of the ring opening of 1,2-Epoxides by means of chelating processes. 11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters
  作者：Francesca Azzena、Paolo Crotti、Lucilla Favero、Mauro Pineschi

  DOI：10.1016/0040-4020(95)00877-b

  日期：1995.11

  The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)(2)].
• A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides
  作者：Giuliana Righi、Giovanna Pescatore、Francesco Bonadies、Carlo Bonini

  DOI：10.1016/s0040-4020(01)00492-6

  日期：2001.6

  The results obtained in the MgBr2-mediated opening of 2,3-bifunctionalized epoxides are reported. The studies showed that the chelation control of MgBr2 between different functionalities can in some cases be selective. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Highly efficient stereoselective synthesis of d-erythro-sphingosine and d-lyxo-phytosphingosine
  作者：Giuliana Righi、Simona Ciambrone、Claudia D'Achille、Andrea Leonelli、Carlo Bonini

  DOI：10.1016/j.tet.2006.08.049

  日期：2006.12

  Starting from a single suitable functionalised epoxide, a highly efficient stereoselective synthesis of d-erythro-sphingosine and d-lyxo-phytosphingosine is described. The approach allows the formal preparation of all stereoisomers of these sphingoid structures.

  从一个单一的合适的官能化环氧化物起始，D-的高效立体选择性合成赤-sphingosine和D-来苏-phytosphingosine进行说明。该方法允许形式上制备这些类神经鞘结构的所有立体异构体。