β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-GlcpNAcOMe | 89255-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-GlcpNAcOMe
• 英文别名: Gal-beta1,4-GlcNAc-beta1,3Gal-beta1,4GlcNAc-beta1,3-Gal-beta1,4GlcNAc-beta1-O-Me；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide
• CAS: 89255-26-5
• 化学式: C₄₃H₇₃N₃O₃₁
• 分子量: 1128.05
• InChiKey: WCFHRGBAIRKQMX-BEAGYCNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.7
• 重原子数：
  77
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  522
• 氢给体数：
  19
• 氢受体数：
  31

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以80%的产率得到β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-β-D-GlcpNAcOMe
  参考文献：
  名称：

  Syntheses of linear tetra-, hexa-, and octa-saccharide fragments of the i-blood group active poly-(N-acetyl-lactosamine) series. Blockwise methods for the synthesis of repetitive oligosaccharide sequences

  摘要：

  N-Phthaloylation of lactosamine gave various glycosyl donors (beta-chloride, beta-trichloroacetimidate) and glycosyl acceptors (3',4'-diol). Coupling of the chloride with a methyl beta-D-glycoside led to the tetrasaccharide fragment, beta-D-Galp-(1----4)-beta-D-GlcpNac-(1----3)-beta-D-Galp-(1----4)- beta-D-GlcpNAcOMe. Acetolysis of the protected tetrasaccharide, followed by treatment with hydrogen chloride, gave a tetrasaccharide chloride which was coupled with the methyl beta-glycoside of lactosamine. A hexasaccharide fragment, [beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)]2-beta-D-Galp-(1----4)-bet a- D-GlcpNAcOMe, was thus obtained by this ("n + 1") method. A more efficient ("n + n") method was applied for the synthesis of an octasaccharide fragment, [beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)]3-beta-D-Galp- (1----4)-beta-D-GlcpNAcOMe (38), where di- and tetra-saccharide intermediates having a 3,4-O-isopropylidene-beta-D-galactopyranosyl nonreducing terminal group and a benzyl beta-D-glycoside group were precursors, either as glycosyl donors (beta-trichloroacetimidates) or glycosyl acceptors (3,4-diols as nonreducing terminal groups). Thus, doubling the length of the repetitive oligosaccharide sequence could be efficiently accomplished at each glycosylation step.

  DOI：

  10.1016/0008-6215(90)80002-k

文献信息

• Block synthesis of a hexasaccharide hapten of i blood group antigen
  作者：Jocelyne Alais、Alain Veyrieres

  DOI：10.1016/s0040-4039(00)88402-6

  日期：1983.1