(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propan-1-ol | 566199-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propan-1-ol
• 英文别名: (2R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylamino]propan-1-ol
• CAS: 566199-88-0
• 化学式: C₁₅H₃₃NO₄Si
• 分子量: 319.517
• InChiKey: QIYFRTCBIVCAEV-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propan-1-ol 在 2,6-二甲基吡啶 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  A new bicyclic proline-mimetic amino acid

  摘要：

  A new constrained bicyclic alpha-amino acid proline-mimetic was developed. The synthesis was achieved starting from derivatives of the chiral pool, thus allowing to prepare analogues of either L- or D-proline by choosing appropriate stereoisomers of serine and alpha,beta-isopropylidene-glycerol derivatives. The scaffolds were prepared as N-Fmoc-amino acid suitable for solid-phase peptide synthesis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00663-4
• 作为产物：
  描述：

  [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate 、 (R)-2-amino-3-((tert-butyldimethylsilyl)oxy)propan-1-ol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propan-1-ol
  参考文献：
  名称：

  A new bicyclic proline-mimetic amino acid

  摘要：

  A new constrained bicyclic alpha-amino acid proline-mimetic was developed. The synthesis was achieved starting from derivatives of the chiral pool, thus allowing to prepare analogues of either L- or D-proline by choosing appropriate stereoisomers of serine and alpha,beta-isopropylidene-glycerol derivatives. The scaffolds were prepared as N-Fmoc-amino acid suitable for solid-phase peptide synthesis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00663-4