2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-β-D-galactopyranoside | 299179-59-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-β-D-galactopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-4-acetyloxy-5-(butanoylamino)-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 299179-59-2
• 化学式: C₃₃H₅₅NO₁₈Si
• 分子量: 781.881
• InChiKey: CIUSRZYSQNXAJK-AUQHTHTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  258.21
• 氢给体数：
  4.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 vanadium(III) fluoride 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 52.0h， 生成 (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-1-O-acetyl-2,4,6-tri-O-benzoyl-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of Sialyl-α-(2→3)-Neolactotetraose Derivatives Containing Different Sialic Acids: Molecular Probes for Elucidation of Substrate Specificity of Human α1,3-Fucosyltransferases

  摘要：

  A series of sialyl-alpha-(2-->3)-neolactotetraose derivatives containing N-acetyl-(NeuAc), N-glycolyl- (NeuGc) and N-butanoylneuraminic acid, and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) have systematically been synthesized as molecular probes for elucidation of substrate specificity of human alpha 1,3-fucosyltransferases (Fuc-TVII and Fuc-TVI). 2-Methyl-(3,4, 6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopylano)-[2',1' :4,5]-2-oxazoline (1) was coupled with 2-(trimethyl-silyl)-ethyl (2,4,6-tri-O-benzyl-beta-D-galactopyranosyl) -(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (2) to give a trisaccharide 3 which, upon successive O-deacetylation, benzylidenation and reductive opening of the benzylidene group, afforded a common glycosyl acceptor 5. Glycosylation of 5 with sialyl-alpha-(2-->3)-galactose donors 6-8, 19 and 21 gave the corresponding pentasaccharides 22-25, which were converted to a series of sialyl-alpha-(2-->3)-neolactotetraose derivatives 30-33. In the competitive enzyme assay, the NeuGc derivative 32 showed the most potent activity for Fuc-TVII, while the KDN derivative 31 was less active than the standard NeuAc derivative 30. In contrast, the N-butanoylation of neuraminic acid enhanced the activity for Fuc-TVI.

  DOI：

  10.1080/07328300008544114
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 Angstroem MS 、 氢气 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Sialyl-α-(2→3)-Neolactotetraose Derivatives Containing Different Sialic Acids: Molecular Probes for Elucidation of Substrate Specificity of Human α1,3-Fucosyltransferases

  摘要：

  A series of sialyl-alpha-(2-->3)-neolactotetraose derivatives containing N-acetyl-(NeuAc), N-glycolyl- (NeuGc) and N-butanoylneuraminic acid, and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) have systematically been synthesized as molecular probes for elucidation of substrate specificity of human alpha 1,3-fucosyltransferases (Fuc-TVII and Fuc-TVI). 2-Methyl-(3,4, 6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopylano)-[2',1' :4,5]-2-oxazoline (1) was coupled with 2-(trimethyl-silyl)-ethyl (2,4,6-tri-O-benzyl-beta-D-galactopyranosyl) -(1 --> 4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside (2) to give a trisaccharide 3 which, upon successive O-deacetylation, benzylidenation and reductive opening of the benzylidene group, afforded a common glycosyl acceptor 5. Glycosylation of 5 with sialyl-alpha-(2-->3)-galactose donors 6-8, 19 and 21 gave the corresponding pentasaccharides 22-25, which were converted to a series of sialyl-alpha-(2-->3)-neolactotetraose derivatives 30-33. In the competitive enzyme assay, the NeuGc derivative 32 showed the most potent activity for Fuc-TVII, while the KDN derivative 31 was less active than the standard NeuAc derivative 30. In contrast, the N-butanoylation of neuraminic acid enhanced the activity for Fuc-TVI.

  DOI：

  10.1080/07328300008544114