isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 1256157-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• CAS: 1256157-11-5
• 化学式: C₄₅H₅₄Cl₃NO₁₄S
• 分子量: 971.347
• InChiKey: VUSOYZMLXUZISD-HGJLHEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  172.61
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 、 4-methoxyphenyl 2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1-2)-[4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-6)]-3,4-O-isopropylidene-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以84%的产率得到4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-α-D-galactopyranosyl-(1-3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-6)-[2-O-benzyl-3,4-O-isopropylidene-α-L-fucopyranosyl-(1-2)]-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the pentasaccharide repeating unit of Escherichia coli O128 antigen

  摘要：

  A pentasaccharide, 4-methoxyphenyl 2-acetamido-2-deoxy-beta-D-galactoPyranosyl-(1 -> 4)-alpha-D-galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-beta-D-galactoPyranosyl-(1 -> 6)-[alpha-L-fucopyranosyl-(1 -> 2)]-beta-D-galactopyranoside (1), representing the repeating unit of Escherichia coli O128 antigen, was successfully prepared in 23% overall yield via a convergent '2+3' glycosylation strategy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.07.025
• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-propan-2-ylsulfanyloxan-3-ol 、 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以73%的产率得到isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the pentasaccharide repeating unit of Escherichia coli O128 antigen

  摘要：

  A pentasaccharide, 4-methoxyphenyl 2-acetamido-2-deoxy-beta-D-galactoPyranosyl-(1 -> 4)-alpha-D-galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-beta-D-galactoPyranosyl-(1 -> 6)-[alpha-L-fucopyranosyl-(1 -> 2)]-beta-D-galactopyranoside (1), representing the repeating unit of Escherichia coli O128 antigen, was successfully prepared in 23% overall yield via a convergent '2+3' glycosylation strategy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.07.025