methyl (β-D-galactopyranosyl-(1-4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 89255-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (β-D-galactopyranosyl-(1-4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl O-β-D-galactopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside；methyl beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-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)-2-methoxyoxan-3-yl]acetamide
• CAS: 89255-25-4
• 化学式: C₂₉H₅₀N₂O₂₁
• 分子量: 762.717
• InChiKey: ZSZNTFKMEGAQIS-SVCFGOAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.9
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  355
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl(1<*>4)-2-deoxy-2-phthalimido-3,6-di-O-acetyl-β-D-glucopyranosyl chloride 在 2,4,6-三甲基吡啶 、 silver trifluoroacetate 作用下， 生成 methyl (β-D-galactopyranosyl-(1-4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Block synthesis of a hexasaccharide hapten of i blood group antigen

  摘要：

  DOI：

  10.1016/s0040-4039(00)88402-6

文献信息

• EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS1
  作者：Therese Buskas、Peter Konradsson、Stefan Oscarson

  DOI：10.1081/car-100108275

  日期：——

  Di-, tri- and tetramers of beta-(1 -->3)-linked N-acetyllactosamine residues have been synthesised as their methyl glycosides, to be used in ITC binding studies to various galectins. The synthetic strategy involves two types of regioselective glycosylations: couplings of a galactosyl donor to 3,4-diol N-tetrachlorophthalimido glucose acceptors to give the lactosamine monomer building blocks, and subsequent formation of the oligomers through consecutive couplings of lactosamine donors to 2',3',4'-lactosamine acceptors, with high selectivity for the desired products.
• 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
  作者：Jocelyne Alais、Alain Veyrie`res

  DOI：10.1016/0008-6215(90)80002-k

  日期：1990.10

  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.
• 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