(R)-N-(tert-butoxycarbonyl)-4-(hydroxy(diphenyl)methyl)-2,2,4-trimethyl-1,3-oxazolidine | 530113-08-7

• 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: (R)-N-(tert-butoxycarbonyl)-4-(hydroxy(diphenyl)methyl)-2,2,4-trimethyl-1,3-oxazolidine
• 英文别名: tert-butyl (4R)-4-[hydroxy(diphenyl)methyl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 530113-08-7
• 化学式: C₂₄H₃₁NO₄
• 分子量: 397.514
• InChiKey: FTCKHPMCHMDAAS-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (R)-N-(tert-butoxycarbonyl)-4-(hydroxy(diphenyl)methyl)-2,2,4-trimethyl-1,3-oxazolidine 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (R)-4-Hydroxymethyl-4-methyl-5,5-diphenyl-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives

  摘要：

  This report describes the synthesis of the two enantiomerically pure a-methylated P-branched phenylalanine derivatives, (S)- and (R)-alpha-methyl-beta,beta-diphenylalanine-(alphaMe)Dip-starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-alpha-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other alpha-methylated beta-branched serine derivatives is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00828-5
• 作为产物：
  描述：

  phenylmagnesium bromide 、 (R)-N-(tert-butoxycarbonyl)-4-methoxycarbonyl-2,2,4-trimethyl-3-oxazolidine 以 四氢呋喃 为溶剂， 以87%的产率得到(R)-N-(tert-butoxycarbonyl)-4-(hydroxy(diphenyl)methyl)-2,2,4-trimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives

  摘要：

  This report describes the synthesis of the two enantiomerically pure a-methylated P-branched phenylalanine derivatives, (S)- and (R)-alpha-methyl-beta,beta-diphenylalanine-(alphaMe)Dip-starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-alpha-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other alpha-methylated beta-branched serine derivatives is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00828-5

文献信息

• Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives
  作者：Alberto Avenoza、Jesús H. Busto、Carlos Cativiela、Jesús M. Peregrina、David Sucunza、Marı́a M. Zurbano

  DOI：10.1016/s0957-4166(02)00828-5

  日期：2003.2

  This report describes the synthesis of the two enantiomerically pure a-methylated P-branched phenylalanine derivatives, (S)- and (R)-alpha-methyl-beta,beta-diphenylalanine-(alphaMe)Dip-starting from the chiral building blocks (R)- and (S)-N-Boc-N,O-isopropylidene-alpha-methylserine methyl esters, respectively. The key step involves a double alkylation with a Grignard reagent on an ester group. The use of the same protocol for the preparation of other alpha-methylated beta-branched serine derivatives is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.