ethyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside | 403832-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-2-ethylsulfanyl-6-(phenylmethoxymethyl)-3-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-4-yl] benzoate
• CAS: 403832-90-6
• 化学式: C₄₉H₄₇Cl₄NO₁₅S
• 分子量: 1063.79
• InChiKey: YMWHHCGMJJLZAX-QZJORRNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  70
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  214
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 、 ethyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 在 3 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以69%的产率得到[(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-[(2S,3R,4R,5S,6R)-4-benzoyloxy-6-(phenylmethoxymethyl)-3-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-methoxy-6-(phenylmethoxymethyl)-3-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-4-yl] benzoate
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS1

  摘要：

  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.

  DOI：

  10.1081/car-100108275
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside 在 吡啶 、 3 A molecular sieve 、 溴 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 ethyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3-O-benzoyl-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS1

  摘要：

  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.

  DOI：

  10.1081/car-100108275