nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 158979-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• CAS: 158979-46-5
• 化学式: C₂₁H₂₆N₂O₁₁
• 分子量: 482.444
• InChiKey: FNKJSZHFINMMKI-PFAUGDHASA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  653.7±55.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  169.6
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic oligosaccharide synthesis on a soluble polymeric carrier

  摘要：

  A facile and efficient method for the chemical and enzymatic syntheses of oligosaccharides using a new type of soluble polymeric sugar acceptor substrate is described. The water soluble glycopolymers having N-acetyl-D-glucosamine (GlcNAc) branches derived from a p-substituted benzyl glycosides were galactosylated with bovine milk galactosyl transferase. The flexible GlcNAc branches of the polymer chains allow quantitative galactosylation and subsequent hydrogenolysis proceeded smoothly to release the desired N-acetyl-lactosamine from the polymer support in high yield.

  DOI：

  10.1016/s0040-4039(00)77272-8
• 作为产物：
  描述：

  对硝基苯甲醇 、 (3aR)-2-甲基-5alpha-(乙酰氧基甲基)-6beta,7alpha-二乙酰氧基-3Aalpha,6,7,7Aalpha-四氢-5H-吡喃并[3,2-d]恶唑 在 camphor-10-sulfonic acid 、 三乙胺 作用下， 生成 nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  High performance polymer supports for enzyme-assisted synthesis of glycoconjugates

  摘要：

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10051-9

文献信息

• Zemlyakov; Kur'yanov; Sidorova, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 551 - 558
  作者：Zemlyakov、Kur'yanov、Sidorova、Chirva

  DOI：——

  日期：——
• Synthesis and modification of spacered glycosides of N-acetylglucosamine
  作者：A. E. Zemlyakov、V. O. Kur'yanov、E. A. Sidorova、T. A. Chupakina、V. Ya. Chirva

  DOI：10.1007/bf02254805

  日期：1997.9