N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-glucopyranosyl)-L-serine benzyl ester | 172325-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-glucopyranosyl)-L-serine benzyl ester
• 英文别名: benzyl N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate；benzyl (2S)-2-(benzhydrylideneamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxypropanoate
• CAS: 172325-20-1
• 化学式: C₃₈H₃₉Cl₃N₂O₁₂
• 分子量: 822.093
• InChiKey: JMOVLTYWKCYOOD-VLVHFTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-glucopyranosyl)-L-serine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

  摘要：

  General glycosidation methodology has been developed which can selectively provide 2acetamido-2-deoxy-alpha- or beta-glycosides of beta-hydroxy-alpha-amino acid derivatives [glucopyranoside- (8, 43), galactopyranoside- (9, 13), mannopyranoside- (10), lactoside analogs (11, 38) and 3-O-beta-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic a-imino esters (Schiff bases) of L-serine and L-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl- or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete H-1- and C-13-NMR data are provided for all compounds.

  DOI：

  10.1016/0008-6215(95)00016-m
• 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 N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-glucopyranosyl)-L-serine 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