D-threonine-O-tert-butyl-N-FMOC benzyl ester | 337903-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: D-threonine-O-tert-butyl-N-FMOC benzyl ester
• 英文别名: benzyl (2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoate
• CAS: 337903-37-4
• 化学式: C₃₀H₃₃NO₅
• 分子量: 487.596
• InChiKey: KGRDAMFCJAHXEG-CCLHPLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-threonine-O-tert-butyl-N-FMOC benzyl ester 在 三氟乙酸 作用下， 反应 2.0h， 以92%的产率得到benzyl N-[9-(fluorenylmethoxycarbonyl)]-D-threoninate
  参考文献：
  名称：

  Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin

  摘要：

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

  DOI：

  10.1021/jo005712m
• 作为产物：
  描述：

  氯甲酸苄酯 、 芴甲氧羰基-O-叔丁基-D-苏氨酸 在 4-二甲氨基吡啶 、 二乙基异丙基胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以87%的产率得到D-threonine-O-tert-butyl-N-FMOC benzyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin

  摘要：

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

  DOI：

  10.1021/jo005712m