8-(Methoxycarbonyl)octyl 2-acetamido-2-deoxy-α-D-mannopyranoside | 143528-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(Methoxycarbonyl)octyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• 英文别名: methyl 9-[(2S,3S,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonanoate
• CAS: 143528-44-3
• 化学式: C₁₈H₃₃NO₈
• 分子量: 391.462
• InChiKey: VPMCTXJWSFZZCE-DEORAPPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 在 甲醇 、 sodium tetrahydroborate 、 乙醇 、 silver silicate 、 4 A molecular sieve 、 sodium methylate 、 nickel dichloride 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 8-(Methoxycarbonyl)octyl 2-acetamido-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates

  摘要：

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.

  DOI：

  10.1016/s0008-6215(00)90517-2

文献信息

• IMMUNOSUPPRESSIVE AND TOLEROGENIC MODIFIED LEWIS?X AND LEWIS?A COMPOUNDS
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0591254A1

  公开（公告）日：1994-04-13
• REDUCING INFLAMMATION BY TIME DEPENDENT ADMINISTRATION OF OLIGOSACCHARIDES GLYCOSIDES RELATED TO BLOOD GROUP DETERMINANTS
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0650492A1

  公开（公告）日：1995-05-03
• US4137401A
  申请人：——

  公开号：US4137401A

  公开（公告）日：1979-01-30
• US4238473A
  申请人：——

  公开号：US4238473A

  公开（公告）日：1980-12-09
• US5580858A
  申请人：——

  公开号：US5580858A

  公开（公告）日：1996-12-03