ethyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside | 403832-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 4,5,6,7-tetrachloro-2-[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 403832-88-2
• 化学式: C₂₃H₂₁Cl₄NO₆S
• 分子量: 581.301
• InChiKey: WJMDDFWBOJMVJG-GDMZHWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 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
• 作为产物：
  描述：

  溴甲苯 、 ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 在 三丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 23.0h， 以67%的产率得到ethyl 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

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.