(2S,3S)-3-(二苄基氨基)-4-苯基丁烷-1,2-二醇 | 200616-22-4

• 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: (2S,3S)-3-(二苄基氨基)-4-苯基丁烷-1,2-二醇
• 英文名称: (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol
• 英文别名: (2S,3S)-3-dibenzylamino-5-phenylbutane-1,2-diol；1,2-Butanediol, 3-[bis(phenylmethyl)amino]-4-phenyl-, (2S,3S)-；(2S,3S)-3-(dibenzylamino)-4-phenylbutane-1,2-diol
• CAS: 200616-22-4
• 化学式: C₂₄H₂₇NO₂
• 分子量: 361.484
• InChiKey: DDKWOBSGZHQFQP-BJKOFHAPSA-N

物化性质

• 沸点：
  553.3±40.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(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：

  (2S,3S)-3-(二苄基氨基)-4-苯基丁烷-1,2-二醇 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.5h， 以1.14 g的产率得到(2S,3S)-3-amino-4-phenylbutane-1,2-diol
  参考文献：
  名称：

  A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

  摘要：

  Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me-2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an alpha-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (+/-)-5,5-dimethyl-1, 3-thiazolidine-4-carboxyl ate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (+/-)-8b in 46% yield for another round of the enzymatic processing. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00257-4
• 作为产物：
  描述：

  苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 双氧水 、 碳酸氢钠 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 (2S,3S)-3-(二苄基氨基)-4-苯基丁烷-1,2-二醇
  参考文献：
  名称：

  A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

  摘要：

  Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me-2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an alpha-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (+/-)-5,5-dimethyl-1, 3-thiazolidine-4-carboxyl ate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (+/-)-8b in 46% yield for another round of the enzymatic processing. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00257-4

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.
• A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors
  作者：Masaya Ikunaka、Jun Matsumoto、Yukifumi Nishimoto

  DOI：10.1016/s0957-4166(02)00257-4

  日期：2002.6

  Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me-2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an alpha-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (+/-)-5,5-dimethyl-1, 3-thiazolidine-4-carboxyl ate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (+/-)-8b in 46% yield for another round of the enzymatic processing. (C) 2002 Elsevier Science Ltd. All rights reserved.