N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-L-serine benzyl ester | 172325-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-L-serine benzyl ester
• CAS: 172325-12-1
• 化学式: C₃₇H₃₈N₄O₁₂
• 分子量: 730.728
• InChiKey: VHSPPZUCLPLXIM-CFHPLBFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  210.75
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-L-serine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 生成 (S)-3-((2S,3S,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-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：

  Fmoc-Ser(3,4,6-Tri-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)-OBzl 在 sodium azide 、 (NH₄)2Ce(NO₃)4 作用下， 以40%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-L-serine benzyl ester
  参考文献：
  名称：

  Kessler, Horst; Kottenhahn, Matthias; Kling, Andreas, Angewandte Chemie, 1987, vol. 99, # 9, p. 919 - 921

  摘要：

  DOI：