(1S,4S,5R)-4-Benzyloxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid 9H-fluoren-9-ylmethyl ester | 566199-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (1S,4S,5R)-4-Benzyloxymethyl-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,4S,5R)-4-(phenylmethoxymethyl)-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylate
• CAS: 566199-94-8
• 化学式: C₂₈H₂₇NO₅
• 分子量: 457.526
• InChiKey: BXNSTCZHSUHBBG-SQMFLSJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4S,5R)-4-Benzyloxymethyl-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 在 jones reagent 、 三氯化铁 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 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：

  O-benzyl-L-serinol 在 2,6-二甲基吡啶 、 三乙酰氧基硼氢化钠 、 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,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