((R)-2-Benzyloxy-1-hydroxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 566199-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ((R)-2-Benzyloxy-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-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-N-[(2R)-1-hydroxy-3-phenylmethoxypropan-2-yl]carbamate
• CAS: 566199-91-5
• 化学式: C₃₁H₃₅NO₆
• 分子量: 517.622
• InChiKey: MSJDMHNTTPHALJ-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 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-Benzyloxy-1-hydroxymethyl-ethyl)-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 在 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (1S,4S,5R)-4-Benzyloxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-carboxylic 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 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-Benzyloxy-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