2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside | 170452-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl (methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside；methyl (2S,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-2-[(2R,3S,4S,5R,6R)-3,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 170452-87-6
• 化学式: C₅₄H₆₅NO₂₃Si
• 分子量: 1124.19
• InChiKey: CBBFFJLVHMRULS-MEIPDKIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  79.0
• 可旋转键数：
  24.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  302.72
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 (methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosulonate)-(2->3)-2,4,6-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  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 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 Angstroem MS 、 氢气 作用下， 以 吡啶 、 溶剂黄146 、 乙腈 为溶剂， 反应 48.0h， 生成 2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-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

文献信息

• Synthesis of a Sialyl Lewis X Ganglioside Analogue Containing<i>N</i>-Glycolyl in Place of the<i>N</i>-Acetyl Group in the<i>N</i>-Acetylneuraminic Acid Residue
  作者：Akira Hasegawa、Akira Uchimura、Hideharu Ishida、Makoto Kiso

  DOI：10.1271/bbb.59.1091

  日期：1995.1

  A sialyl Lewis X ganglioside analogue containing 5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid in place of N-acetylneurarninic acid was synthesized, clarifying the structural requirement for an N-acetyl group in the sialic acid moiety for selectin recognition.

  合成了一种含有 5-甘氨酰氨基-3,5-二脱氧-D-甘油-D-半乳糖-2-nonulopyranosylonic 酸而不是 N-acetylneurarninic 酸的 sialyl Lewis X 神经节苷脂类似物，明确了选择素识别中对 sialic 酸分子中 N-acetyl 基团的结构要求。