2-(trimethylsilyl)ethyl (β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 500720-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 500720-78-5
• 化学式: C₆₅H₈₀O₁₆Si
• 分子量: 1145.43
• InChiKey: RBMANWAFNHMENJ-SQPKFTRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  82.0
• 可旋转键数：
  29.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  191.68
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium hydroxide 、 四丁基硫酸氢铵 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2-(trimethylsilyl)ethyl (3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS OF SIALYL-α-(2→3)-NEOLACTOTETRAOSE DERIVATIVES MODIFIED AT C-2 OF THEN-ACETYLGLUCOSAMINE RESIDUE: PROBES FOR INVESTIGATION OF ACCEPTOR SPECIFICITY OF HUMAN α-1,3-FUCOSYLTRANSFERASES, FUC-TVII, AND FUC-TVI^*

  摘要：

  A variety of sialyl-alpha-(2-->3)-neolactotetraose (IV3 NeuAcnLcOse(4) or IV(3)NeuGcnLcOse(4)) derivatives (23, 31-37, 58-60) modified at C-2 of the GlcNAc: residue have been synthesized. The phthalimido group at C-2 of GlcNAc in 2-(trimethylsilyl)ethyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1-->3)-(2,4,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (5) was systematically converted to a series of acylamino groups, to give the per-O-benzylated trisaccharide acceptors (6-11). On the other hand, modification of the hydroxyl group at C-2 of the terminal Glc residue in 2-(trimethylsilyl)ethyl (4,6-O-benzylidene-beta-D-glucopyranosyl)-(1-->3)-(2,4,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (42) gave three different kinds of trisaccharide acceptors containing D-glucose (49), N-acetyl-D-mannosamine (50), and D-mannose (51) instead of the GlcNAc residue. Totally ten trisaccharide acceptors (5-11 and 49-51) were each coupled with sialyl-alpha-(2-->3)-galactose donor 12 to afford the corresponding pentasaccharides (14-21 and 52-54) in good yields, respectively, which were then transformed into the target compounds. Acceptor specificity of the synthetic sialyl-alpha-(2-->3)-neolactotetraose probes for the human alpha-(1-->3)-fucosyltransferases, Fuc-TVII and Fuc-TVI, was examined.

  DOI：

  10.1081/car-120014902
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以97%的产率得到2-(trimethylsilyl)ethyl (β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS OF SIALYL-α-(2→3)-NEOLACTOTETRAOSE DERIVATIVES MODIFIED AT C-2 OF THEN-ACETYLGLUCOSAMINE RESIDUE: PROBES FOR INVESTIGATION OF ACCEPTOR SPECIFICITY OF HUMAN α-1,3-FUCOSYLTRANSFERASES, FUC-TVII, AND FUC-TVI^*

  摘要：

  A variety of sialyl-alpha-(2-->3)-neolactotetraose (IV3 NeuAcnLcOse(4) or IV(3)NeuGcnLcOse(4)) derivatives (23, 31-37, 58-60) modified at C-2 of the GlcNAc: residue have been synthesized. The phthalimido group at C-2 of GlcNAc in 2-(trimethylsilyl)ethyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1-->3)-(2,4,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (5) was systematically converted to a series of acylamino groups, to give the per-O-benzylated trisaccharide acceptors (6-11). On the other hand, modification of the hydroxyl group at C-2 of the terminal Glc residue in 2-(trimethylsilyl)ethyl (4,6-O-benzylidene-beta-D-glucopyranosyl)-(1-->3)-(2,4,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (42) gave three different kinds of trisaccharide acceptors containing D-glucose (49), N-acetyl-D-mannosamine (50), and D-mannose (51) instead of the GlcNAc residue. Totally ten trisaccharide acceptors (5-11 and 49-51) were each coupled with sialyl-alpha-(2-->3)-galactose donor 12 to afford the corresponding pentasaccharides (14-21 and 52-54) in good yields, respectively, which were then transformed into the target compounds. Acceptor specificity of the synthetic sialyl-alpha-(2-->3)-neolactotetraose probes for the human alpha-(1-->3)-fucosyltransferases, Fuc-TVII and Fuc-TVI, was examined.

  DOI：

  10.1081/car-120014902