正庚基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷 | 115431-24-8

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 正庚基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷
• 中文别名: 七烷基-2,3,4,6-四-氧-乙酰基-β-D-吡喃氨基葡萄糖苷；七烷基-2,3,4,6-四-氧-乙酰基-Β-D-吡喃氨基葡萄糖苷；正庚基2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷
• 英文名称: heptyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: heptyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside；Heptyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-heptoxyoxan-2-yl]methyl acetate
• CAS: 115431-24-8
• 化学式: C₂₁H₃₅NO₉
• 分子量: 445.51
• InChiKey: RBCLSYRDYAVQGI-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  正庚基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷 在 N-羟基丁二酰亚胺 、 硫酸 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.08h， 生成 O-(heptyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine γ-benzyl ester
  参考文献：
  名称：

  Synthesis of glycosidic analogues of N-acetylneuramoyl-L-alanyl-D-isoglutamine

  摘要：

  DOI：

  10.1007/bf00598682
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 potassium carbonate 、 cobalt(II) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 正庚基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Glycosylated derivatives of substituted hydroxylamine. II. The phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine

  摘要：

  The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis acids resulted in alkyl-O-glucosaminides with the 1,2-trans-configuration of the glycoside bond. Other glucosaminides of substituted hydroxylamine were shown not to react under these conditions. The structures of the synthesized glucosaminides were confirmed by H-1 NMR spectroscopy and comparison with the authentic compounds.

  DOI：

  10.1134/s1068162013030084

文献信息

• Synthesis of?-glycosides of n-acetylglucosamine in the presence of HgI2
  作者：A. E. Zemlyakov、V. O. Kur'yanov、V. Ya. Chirva

  DOI：10.1007/bf01372338

  日期：1996.5
• US4563445A
  申请人：——

  公开号：US4563445A

  公开（公告）日：1986-01-07
• Glycosylated derivatives of substituted hydroxylamine. II. The phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine
  作者：V. O. Kuryanov、A. A. Luschtshyk、T. A. Chupakhina

  DOI：10.1134/s1068162013030084

  日期：2013.7

  The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis acids resulted in alkyl-O-glucosaminides with the 1,2-trans-configuration of the glycoside bond. Other glucosaminides of substituted hydroxylamine were shown not to react under these conditions. The structures of the synthesized glucosaminides were confirmed by H-1 NMR spectroscopy and comparison with the authentic compounds.
• Synthesis of glycosidic analogues of N-acetylneuramoyl-L-alanyl-D-isoglutamine
  作者：A. E. Zemyakov、V. Ya. Chirva

  DOI：10.1007/bf00598682

  日期：1987.9