(2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol | 474022-71-4

• 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: (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol
• 英文别名: (2S,3S)-3-(dibenzylamino)-1-[dimethyl(propan-2-yloxy)silyl]-4-phenylbutan-2-ol
• CAS: 474022-71-4
• 化学式: C₂₉H₃₉NO₂Si
• 分子量: 461.72
• InChiKey: PFBVLTMAEOYIOY-URLMMPGGSA-N

物化性质

• 沸点：
  556.3±50.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol 在 palladium on activated charcoal 氢气 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 (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：

  氯甲基二甲基异丙氧基硅烷 、 苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol
  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

• 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.