O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyltrichloracetimidat | 129750-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyltrichloracetimidat
• 英文别名: Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b1-2)Man3Ac4Ac6Ac(a)-O-C(NH)CCl3；[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-6-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 129750-36-3
• 化学式: C₄₀H₅₃Cl₃N₂O₂₅
• 分子量: 1068.22
• InChiKey: VCGNBUBSVRCLOV-ZWHHFFDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  70
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  345
• 氢给体数：
  2
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->4)-O-(2-O-benzyl-6-O-chloracetyl-β-D-mannopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-desoxy-β-D-glucopyranose 、 O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyltrichloracetimidat 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以19%的产率得到O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->4)>-O-...
  参考文献：
  名称：

  Verzweigten Nonasaccharid-sequenz der“二等分”合成糖蛋白

  摘要：

  一个高度分支的九糖，β-D-半乳糖-（1 ---- 4）-β-D-GlcpNAc-（1 ---- 2）-α-D-Manp-（1 ---- 3）- [beta-D-Glcp-NAc-（1 ---- 4）-[beta-D-Galp-（1 ---- 4）-beta-D-GlcpNAc-（1 ---- 2）-alpha -D- Manp-（1 ---- 6）]-beta-D-Manp-（1 ---- 4）-D-GlcNAc，代表N型乳糖胺“对分”结构的碳水化合物链-糖蛋白通过嵌段合成方法合成。活化的三糖嵌段β-D-Galp-（1 ---- 4）-β-D-GlcpNAc-（1 ---- 2）-D-Man首先与低反应性OH-3基团偶联，在第二步中，在适当保护的三糖嵌段内的中心β-D-甘露吡喃糖基残基的反应性OH-6基团β-D-GlcpNAc-（1 ---- 4）-β-D-Manp-（1 ---- 4）-D-GlcNAc。在这些耦合步骤中，

  DOI：

  10.1016/0008-6215(90)84187-y
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-5-acetylamino-6-((2R,3S,4S,5R,6R)-2,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-3-yloxy)-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 ammonium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyltrichloracetimidat
  参考文献：
  名称：

  Chemoenzymatic synthesis of the branched oligosaccharides which correspond to the core structures of N-linked sugar chains

  摘要：

  Synthetic routes are described to a partial structure common to all high mannose-type sugar chains and complex-type sugar chains based on a chemoenzymatic strategy which incorporates, (a) enzymatic synthesis of oligosaccharide blocks using glycosidases, and (b) chemical synthesis of the branching oligosaccharides via regioselective coupling. All reaction products correspond to key intermediates necessary for the construction of N-linked oligosaccharides and we have synthesized the branched tetra-manno-oligosaccharide high mannose-type sugar chain and the branched hexa-oligosaccharide complex-type sugar chain using this simple and direct method. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10001-5

文献信息

• PAULSEN, HANS;HEUME, MATTHIAS;NURNBERGER, HELGA, CARBOHYDR. RES., 200,(1990) C. 127-166
  作者：PAULSEN, HANS、HEUME, MATTHIAS、NURNBERGER, HELGA

  DOI：——

  日期：——