O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester | 172325-09-6

• 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: O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester
• 英文别名: benzyl (2S)-3-[(2S,3R,4R,5S,6R)-4-acetyloxy-6-(acetyloxymethyl)-3-azido-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-aminopropanoate
• CAS: 172325-09-6
• 化学式: C₃₄H₄₄N₄O₁₈
• 分子量: 796.739
• InChiKey: CGMRKLDQRNKEKA-SBNDPXHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  56
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  261
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 0.75h， 生成 (S)-3-[(2S,3R,4R,5S,6R)-4-Acetoxy-6-acetoxymethyl-3-amino-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
  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：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide 在 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.08h， 生成 O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester
  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