(1S,4R,5R)-4-Hydroxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid 9H-fluoren-9-ylmethyl ester | 566200-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (1S,4R,5R)-4-Hydroxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl (1S,4R,5R)-4-(hydroxymethyl)-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylate
• CAS: 566200-01-9
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: RHCBCKIKZOEIFE-CJMONDIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4R,5R)-4-Hydroxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 在 jones reagent 作用下， 以 丙酮 为溶剂， 以55%的产率得到(1S,4S,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：

  (S)-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 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (1S,4R,5R)-4-Hydroxymethyl-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

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.