(2R,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol | 200616-26-8

• 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,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol
• 英文别名: (2R,3S)-3-(Dibenzylamino)-4-phenylbutane-1,2-diol
• CAS: 200616-26-8
• 化学式: C₂₄H₂₇NO₂
• 分子量: 361.484
• InChiKey: DDKWOBSGZHQFQP-ZEQRLZLVSA-N

物化性质

• 沸点：
  553.303±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.156±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol 在 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R)-[1'(S)-(dibenzylamino)-2'-phenylethyl]oxirane
  参考文献：
  名称：

  An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane

  摘要：

  A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. it involves the diastereoselective reduction of the carbonyl group of gamma-N,N-dibenzyl amino a-hydroxy beta-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.134
• 作为产物：
  描述：

  (4R,1'S)-4-[1'-(dibenzylamino)-2'-(phenyl)ethyl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以92%的产率得到(2R,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol
  参考文献：
  名称：

  Totally Selective Ring-Opening of Amino Epoxides with Ketones:  A General Entry to Enantiopure (2R,3S)- and (2S,3S)-3-Aminoalkano-1,2-diols

  摘要：

  Transformation of enantiopure diastereoisomers (2R,1'S)- and (2S,1'S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of (BF3Et2O)-Et-.. The conversion takes place in very high yields. total selectivity, and without epimerization. A mechanism to explain this transformation is proposed. The obtained 1.3-dioxolanes can be deprotected. and (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols were isolated.

  DOI：

  10.1021/ol047785o

文献信息

• Totally Selective Ring-Opening of Amino Epoxides with Ketones:  A General Entry to Enantiopure (2<i>R</i>,3<i>S</i>)- and (2<i>S</i>,3<i>S</i>)-3-Aminoalkano-1,2-diols
  作者：José M. Concellón、José Ramón Suárez、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1021/ol047785o

  日期：2005.1.1

  Transformation of enantiopure diastereoisomers (2R,1'S)- and (2S,1'S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of (BF3Et2O)-Et-.. The conversion takes place in very high yields. total selectivity, and without epimerization. A mechanism to explain this transformation is proposed. The obtained 1.3-dioxolanes can be deprotected. and (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols were isolated.
• An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane
  作者：Takayuki Suzuki、Yutaka Honda、Kunisuke Izawa

  DOI：10.1016/j.tetlet.2005.06.134

  日期：2005.8

  A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. it involves the diastereoselective reduction of the carbonyl group of gamma-N,N-dibenzyl amino a-hydroxy beta-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield. (c) 2005 Elsevier Ltd. All rights reserved.