benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 875712-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 875712-81-5
• 化学式: C₆₁H₇₃NO₃₃
• 分子量: 1348.24
• InChiKey: VEKICXYYDSRLEB-ACEXPHDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  95.0
• 可旋转键数：
  25.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  420.75
• 氢给体数：
  1.0
• 氢受体数：
  33.0

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 乙二胺 、 乙酸酐 、 三乙胺 作用下， 以 乙醇 、 甲醇 为溶剂， 反应 23.0h， 以86.5%的产率得到benzyl O-β-D-galactopyranosyl-(1->3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the 3-sulfated Lewisa pentasaccharide

  摘要：

  The sulfated pentasaccharide benzyl O-(3-O-sulfo-beta-D-galactopyranosyl)-(1 -> 3)-O-[(alpha-L-fucopyranosyl)-(1 -> 4)]-O-(2-acetamido -2-deoxy-beta-D-glucopyranosyl)-(1 -> 3)-O-(beta-D-galactopyranosyl)-(1 -> 4)-O-beta-D-glucopyranoside sodium salt was synthesized using a chemo-enzymatic approach. Lacto-N-tetraose, obtained from two disaccharides [4-metboxybenzyl O-(2,3,4,6-tetra- O-acetyl-beta-D-galactopranosyl)-(1 -> 3)-4,6-O-benzylidene-2-deoxy-2-phtalimido-beta-D-glucopyranoside and benzyl 2,6-di-O-acetyl -beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri -O-acetyl-beta-D-glucopyranoside], was regioselectively sulfated at the 3 OH position of the terminal galactose using the stannylene procedure. The fucosylation of the sulfated tetrasaccharide was performed using soluble or immobilized fucosyltransferase FucT-III to give the title compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.004
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 、 benzyl O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以50%的产率得到benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the 3-sulfated Lewisa pentasaccharide

  摘要：

  The sulfated pentasaccharide benzyl O-(3-O-sulfo-beta-D-galactopyranosyl)-(1 -> 3)-O-[(alpha-L-fucopyranosyl)-(1 -> 4)]-O-(2-acetamido -2-deoxy-beta-D-glucopyranosyl)-(1 -> 3)-O-(beta-D-galactopyranosyl)-(1 -> 4)-O-beta-D-glucopyranoside sodium salt was synthesized using a chemo-enzymatic approach. Lacto-N-tetraose, obtained from two disaccharides [4-metboxybenzyl O-(2,3,4,6-tetra- O-acetyl-beta-D-galactopranosyl)-(1 -> 3)-4,6-O-benzylidene-2-deoxy-2-phtalimido-beta-D-glucopyranoside and benzyl 2,6-di-O-acetyl -beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri -O-acetyl-beta-D-glucopyranoside], was regioselectively sulfated at the 3 OH position of the terminal galactose using the stannylene procedure. The fucosylation of the sulfated tetrasaccharide was performed using soluble or immobilized fucosyltransferase FucT-III to give the title compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.004