benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate | 150631-07-5

• 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-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate
• 英文别名: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 150631-07-5
• 化学式: C₄₀H₄₁Cl₃N₂O₁₄
• 分子量: 880.13
• InChiKey: QEYHHIMTTBMHSZ-USPNOIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  59
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  200
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate 在 palladium on activated charcoal 氢气 、 锌 作用下， 以 甲醇 为溶剂， 反应 14.5h， 生成 N-(9-fluorenylmethoxycarbonyl)-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-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-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 4 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 22.0h， 生成 benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-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

• Glycoside synthesis via electrophile-induced activation of N-allyl carbamates
  作者：Horst Kunz、Jörg Zimmer

  DOI：10.1016/s0040-4039(00)60478-1

  日期：1993.4

  O-Benzyl-, O-acyl-, N-acyl- and isopropylidene-protected glycosyl N-allylcarbamates, obtained from anomerically unprotected monosaccharides and allyl isocyanate, are activated by an electrophile-induced cyclisation and react with hydroxyl compounds to form the corresponding glycosides.

  由未保护的单糖和异氰酸烯丙酯得到的O-苄基，O-酰基，N-酰基和异亚丙基保护的糖基N-烯丙基氨基甲酸酯，通过亲电试剂诱导的环化反应活化，并与羟基化合物反应形成相应的糖苷。