benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serinate | 337903-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serinate
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-dibenzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-phenylmethoxypropoxy]oxan-2-yl]methyl benzoate
• CAS: 337903-75-0
• 化学式: C₅₄H₄₈N₂O₁₃
• 分子量: 932.981
• InChiKey: GUDQCHQPHVKGIV-BDDVRNCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  69
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serinate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以0.160 g的产率得到N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serine
  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：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 4 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 、 碳酸氢钠 、 锌 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 42.0h， 生成 benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serinate
  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

文献信息

• Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin
  作者：Scott A. Mitchell、Matt R. Pratt、Victor J. Hruby、Robin Polt

  DOI：10.1021/jo005712m

  日期：2001.4.1

  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.