(3S,4S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid methyl ester | 638211-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid methyl ester
• 英文别名: methyl (3S,4S)-3-amino-4-[tert-butyl(diphenyl)silyl]oxypentanoate
• CAS: 638211-36-6
• 化学式: C₂₂H₃₁NO₃Si
• 分子量: 385.579
• InChiKey: LFMGQHZVMKVBIC-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid methyl ester 在 potassium carbonate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 41.0h， 生成 (3S,4S)-3-Dibenzylamino-4-hydroxy-pentanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines

  摘要：

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.

  DOI：

  10.1021/jo035224p
• 作为产物：
  描述：

  (S)-2-(叔丁基二苯基硅氧基)丙醛 在 盐酸 、 titanium(IV) tetraethanolate 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 22.0h， 生成 (3S,4S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines

  摘要：

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.

  DOI：

  10.1021/jo035224p

文献信息

• Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to <i>N</i>-<i>tert</i>-Butanesulfinyl α-Alkoxyaldimines
  作者：Jared W. Evans、Jonathan A. Ellman

  DOI：10.1021/jo035224p

  日期：2003.12.1

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.