methyl 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-1-thio-β-D-galactopyranoside | 170452-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 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-1-thio-β-D-galactopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-2-[(2R,3S,4S,5R,6S)-3,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-methylsulfanyloxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 170452-89-8
• 化学式: C₅₀H₅₅NO₂₂S
• 分子量: 1054.05
• InChiKey: DZNZBEOLTYPKCJ-NZRKYYPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  74
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  319
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 、 methyl 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-1-thio-β-D-galactopyranoside 在 3 A molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到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)-O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-O-(2...
  参考文献：
  名称：

  Synthesis of a Sialyl Lewis X Ganglioside Analogue ContainingN-Glycolyl in Place of theN-Acetyl Group in theN-Acetylneuraminic Acid Residue

  摘要：

  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。

  DOI：

  10.1271/bbb.59.1091
• 作为产物：
  描述：

  methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 methyl 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-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Sialyl Lewis X Ganglioside Analogue ContainingN-Glycolyl in Place of theN-Acetyl Group in theN-Acetylneuraminic Acid Residue

  摘要：

  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。

  DOI：

  10.1271/bbb.59.1091

文献信息

• Synthesis of Sialyl-α-(2→3)-Neolactotetraose Derivatives Containing Different Sialic Acids: Molecular Probes for Elucidation of Substrate Specificity of Human α1,3-Fucosyltransferases
  作者：Eiji Tanahashi、Kyoko Fukunaga、Yuko Ozawa、Tsuyoshi Toyoda、Hidcharu Ishida、Makoto Kiso

  DOI：10.1080/07328300008544114

  日期：2000.1

  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.