[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 566199-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2R)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypropan-2-yl]-N-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 566199-89-1
• 化学式: C₃₀H₄₃NO₆Si
• 分子量: 541.76
• InChiKey: MLHTVPWUYYKZDM-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 在 jones reagent 、 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 (1S,4R,5R)-6,8-Dioxa-3-aza-bicyclo[3.2.1]octane-3,4-dicarboxylic acid 3-(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：

  (R)-2-amino-3-((tert-butyldimethylsilyl)oxy)propan-1-ol 在 2,6-二甲基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-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

文献信息

• A new bicyclic proline-mimetic amino acid
  作者：Andrea Trabocchi、Nicoletta Cini、Gloria Menchi、Antonio Guarna

  DOI：10.1016/s0040-4039(03)00663-4

  日期：2003.4

  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.