methyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-tetrachlorophthaimido-β-D-glucopyranoside | 403833-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-tetrachlorophthaimido-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3S,4R,5R,6R)-4-hydroxy-6-methoxy-2-(phenylmethoxymethyl)-5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)oxan-3-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 403833-01-2
• 化学式: C₄₁H₄₁Cl₄NO₁₅
• 分子量: 929.586
• InChiKey: HCDUVYRRYIESDY-ROXBMGJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-tetrachlorophthaimido-β-D-glucopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以97%的产率得到methyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-tetrachlorophthaimido-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
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 溴 、 三乙基硅基三氟甲磺酸酯 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-tetrachlorophthaimido-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