5-<(benzyloxycarbonyl)amino>pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 142825-49-8

• 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: 5-<(benzyloxycarbonyl)amino>pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 5-benzyloxycarbonylaminopentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[5-(phenylmethoxycarbonylamino)pentoxy]oxan-2-yl]methyl acetate
• CAS: 142825-49-8
• 化学式: C₂₇H₃₇NO₁₂
• 分子量: 567.59
• InChiKey: SNYKNMIBRZNLSD-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-<(benzyloxycarbonyl)amino>pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 生成 (2,3,4,5,6-pentafluorophenyl) (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-[5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoate
  参考文献：
  名称：

  Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates

  摘要：

  Several neoglycosyl amino acids possessing a sugar residue, a spacer and trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodology is useful for application in combinatorial syntheses of neoglycoconjugates as potential mimics for oligosaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00212-4
• 作为产物：
  描述：

  5-(Z-氨基)-1-戊醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 calcium sulfate 、 silver carbonate 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以30%的产率得到5-<(benzyloxycarbonyl)amino>pentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies toward pyruvate acetal-containing saccharides: En route to the efficient synthesis of Rhizobium-related exopolysaccharide fragments

  摘要：

  The disaccharide building block benzyl O-{2,3-di-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl) ethylidene]-beta-D-galactopyranosyl}-(1 --> 3)-2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene] -alpha-D-glucopyranoside (13), related to a Rhizobium exopolysaccharide, was prepared by coupling various 4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-D-galactosyl donors (benzoyl-protected chloride 1, pivaloyl-protected chloride 2, and benzoyl-protected fluorides 3 and 4, and trichloroacetimidate 5) with benzyl 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-alpha-D-glucopyranoside (10) and the corresponding 2,3-O-tetraisopropyldisiloxane-protected glucoside 12. The best results, with respect to beta-selectivity and yield of the coupling, were obtained with 5 and 10 in dichloromethane. The beta-linked (13) and alpha-linked (14) disaccharides were efficiently converted via the 1-OH derivatives 17 and 21 into the corresponding trichloroacetimidates 18 and 22. The latter were used for the synthesis of the disaccharide ligands 4,6-(R)-pyruvate-beta-D-Galp-(1 --> 3)-4,6-(S)-pyruvate-beta-D-Glcp-O (CH2)(5)NH2 (20), and 4,6-(R)-pyruvate-alpha-D-Galp-(1 --> 3)-4,6-(S)-pyruvate-beta-D-Glcp-O(CH2)(5)NH2 (24). The corresponding tri- and tetra-saccharide derivatives 4,6-(R)-pyruvate-beta-D-Galp-(1 --> 3)-4,6-(S)-pyruvate-beta-D-Glcp-(1 --> 4)-beta-D-Glcp-O(CH2)(5)NH2 (28) and 4,6-(R)-pyruvate-beta-D-Galp-(1 --> 3)-4,6-(S)-pyruvate-beta-D-Glcp-(1 --> 4)-beta-D-Glcp-(1 --> 4)-beta-D-Glcp-O(CH2)(5)NH2 (36) were obtained similarly.

  DOI：

  10.1016/s0008-6215(05)80010-2

文献信息

• US5243037A
  申请人：——

  公开号：US5243037A

  公开（公告）日：1993-09-07
• US5342772A
  申请人：——

  公开号：US5342772A

  公开（公告）日：1994-08-30
• US5384254A
  申请人：——

  公开号：US5384254A

  公开（公告）日：1995-01-24
• US5491083A
  申请人：——

  公开号：US5491083A

  公开（公告）日：1996-02-13