(4R,1'S,2'R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-hydroxy-2-methyl-3-buten-1-yl)-1,3-oxazolidine | 178455-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,1'S,2'R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-hydroxy-2-methyl-3-buten-1-yl)-1,3-oxazolidine
• 英文别名: tert-butyl (4R)-4-[(1S,2R)-1-hydroxy-2-methylbut-3-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 178455-17-9
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: NQISHCOEZVDOKR-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,1'S,2'R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-hydroxy-2-methyl-3-buten-1-yl)-1,3-oxazolidine 在 咪唑 、 sodium hydroxide 、 正丁基锂 、 硼烷 、 氨 、 双氧水 、 sodium 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (R)-4-[(Z)-(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-hex-4-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of γ-branched amino acids. TiCl4 Mediated addition of (E)-crotylsilane to N,O-protected serine aldehyde

  摘要：

  The N-Boc derivatives of (2S,3S,4R,6E)-2-amino-3-hydroxy-4-methyl-6-octenoic acid and (2S,4R)-2-amino-4-methyl-hexanoic acid have been prepared using the acetonide of D-Serine aldehyde 1 as a formyl glycine equivalent. The stereochemistry of the y-branch was introduced by reaction of (E)-crotyltrimethylsilane with 1 in the presence of TiCl4 followed by elaboration of the terminal double bond and further transformation of the Serine hydroxymethyl group into a carboxylic acid. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00128-0
• 作为产物：
  描述：

  (E)-but-2-en-1-yltrimethylsilane 、 (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 三氟化硼乙醚 作用下， 生成 5-(tert-butoxycarbonylamino)-3-methyl-1-hexen-4,6-diol 、 (4R,1'S,2'R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-hydroxy-2-methyl-3-buten-1-yl)-1,3-oxazolidine
  参考文献：
  名称：

  Stereocontrolled synthesis of γ-branched amino acids. TiCl4 Mediated addition of (E)-crotylsilane to N,O-protected serine aldehyde

  摘要：

  The N-Boc derivatives of (2S,3S,4R,6E)-2-amino-3-hydroxy-4-methyl-6-octenoic acid and (2S,4R)-2-amino-4-methyl-hexanoic acid have been prepared using the acetonide of D-Serine aldehyde 1 as a formyl glycine equivalent. The stereochemistry of the y-branch was introduced by reaction of (E)-crotyltrimethylsilane with 1 in the presence of TiCl4 followed by elaboration of the terminal double bond and further transformation of the Serine hydroxymethyl group into a carboxylic acid. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00128-0

文献信息

• Stereocontrolled synthesis of γ-branched amino acids. TiCl4 Mediated addition of (E)-crotylsilane to N,O-protected serine aldehyde
  作者：Fabiana D'Aniello、Massimo Falorni、André Mann、Maurizio Taddei

  DOI：10.1016/0957-4166(96)00128-0

  日期：1996.4

  The N-Boc derivatives of (2S,3S,4R,6E)-2-amino-3-hydroxy-4-methyl-6-octenoic acid and (2S,4R)-2-amino-4-methyl-hexanoic acid have been prepared using the acetonide of D-Serine aldehyde 1 as a formyl glycine equivalent. The stereochemistry of the y-branch was introduced by reaction of (E)-crotyltrimethylsilane with 1 in the presence of TiCl4 followed by elaboration of the terminal double bond and further transformation of the Serine hydroxymethyl group into a carboxylic acid. Copyright (C) 1996 Elsevier Science Ltd