methyl 2R-(3'S-(Fmoc)amino-4'S-hydroxy-2'-oxopyrrolidin-1'-yl)-4-methylpentanoate | 1246296-77-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2R-(3'S-(Fmoc)amino-4'S-hydroxy-2'-oxopyrrolidin-1'-yl)-4-methylpentanoate
• 英文别名: methyl (2R)-2-[(3S,4S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-oxopyrrolidin-1-yl]-4-methylpentanoate
• CAS: 1246296-77-4
• 化学式: C₂₆H₃₀N₂O₆
• 分子量: 466.534
• InChiKey: OLZKBXSNSNBXJS-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-亮氨酸甲酯 、 2,2,2-三氟乙醇 、 [9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester 在 间氯过氧苯甲酸 、 苯甲酸 作用下， 以 1,2-二氯乙烷 、 二氯甲烷 为溶剂， 以73%的产率得到methyl 2R-(3'S-(Fmoc)amino-4'R-hydroxy-2'-oxopyrrolidin-1'-yl)-4-methylpentanoate
  参考文献：
  名称：

  α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation

  摘要：

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.

  DOI：

  10.1021/ol1000582

文献信息

• [EN] PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE GAMMA-LACTAMES AMINO-SUBSTITUÉS
  申请人：VALORISATION RECH SOC EN COMMA

  公开号：WO2010105367A1

  公开（公告）日：2010-09-23

  The present application describes general process for the preparation of amino-substitued gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substitued gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

  本申请描述了一般的氨基取代γ-内酰胺的制备过程，涉及到通式(I)和(VI)的合成子与胺的反应。这些过程适用于固相合成技术，因此可以有效地将氨基取代γ-内酰胺并入各种结构支架中，特别是肽类结构。
• α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation
  作者：Daniel J. St-Cyr、Andrew G. Jamieson、William D. Lubell

  DOI：10.1021/ol1000582

  日期：2010.4.16

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.