2-(Tetradecyl)hexadecyl O-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside | 178872-88-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(Tetradecyl)hexadecyl O-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside
• CAS: 178872-88-3
• 化学式: C₈₁H₁₂₇NO₃₀
• 分子量: 1594.89
• InChiKey: LWQPCMYBDUKTPC-VPVBDYPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.25
• 重原子数：
  112.0
• 可旋转键数：
  50.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  386.17
• 氢给体数：
  2.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  3-(二乙氨基)-1,5-二氢-2,4,3-苯并二噁磷杂庚英 、 2-(Tetradecyl)hexadecyl O-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以69%的产率得到2-(Tetradecyl)hexadecyl O-[4,6-di-O-acetyl-2-O-benzoyl-3-O-(o-xylylenedioxyphosphinyl)-β-D-galactopyranosyl]-(1->4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-...
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 85: Synthesis of Sialyl Lewis X Ganglioside Analogs Containing a Variety of Anionic Substituents in Place of Sialic Acid

  摘要：

  Three sialyl-Le(X) ganglioside analogs containing carboxymethyl, sulfate, and phosphate groups in place of the sialic acid moiety, have been synthesized. Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,3-tri-O-benzyl-alpha-L-fucopyranosyl)-(1 --> 3) -O- (2-acetamido-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl) - (1 --> 3) - 2,4,6-tri-O-benzyl-beta-D-galactopyranoside (10) with methyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-1-thio-beta-D-galactopyranoside (6) or methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-beta-D-galactopyranoside (9) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding tetrasaccharide derivatives 11 and 19. Compounds 11 and 19 were converted into the alpha-trichloroacetimidates 14 and 23, via reductive removal of the benzyl and benzylidene groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (15) or 2-(tetradecyl)hexadecan-1-ol (24), gave the lipophilic derivatives 16 and 25. Compound 16 was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound 18 in good yield. Compound 25 was treated with hydrazine acetate to give compound 26, which in turn was transformed, via sulfation or phosphorylation, and O-deacylation, into the target compounds 28 and 31.

  DOI：

  10.1080/07328309608005662
• 作为产物：
  描述：

  2-(Tetradecyl)hexadecyl O-(4,6-di-O-acetyl-2-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyrano... 在 乙酸肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到2-(Tetradecyl)hexadecyl O-(4,6-di-O-acetyl-2-O-benzoyl-β-D-galactopyranosyl)-(1->4)-O-[(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)]-O-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic Studies on Sialoglycoconjugates 85: Synthesis of Sialyl Lewis X Ganglioside Analogs Containing a Variety of Anionic Substituents in Place of Sialic Acid

  摘要：

  Three sialyl-Le(X) ganglioside analogs containing carboxymethyl, sulfate, and phosphate groups in place of the sialic acid moiety, have been synthesized. Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,3-tri-O-benzyl-alpha-L-fucopyranosyl)-(1 --> 3) -O- (2-acetamido-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl) - (1 --> 3) - 2,4,6-tri-O-benzyl-beta-D-galactopyranoside (10) with methyl 2,4,6-tri-O-benzoyl-3-O-(methoxycarbonyl)methyl-1-thio-beta-D-galactopyranoside (6) or methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-beta-D-galactopyranoside (9) using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, afforded the corresponding tetrasaccharide derivatives 11 and 19. Compounds 11 and 19 were converted into the alpha-trichloroacetimidates 14 and 23, via reductive removal of the benzyl and benzylidene groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, and treatment with trichloroacetonitrile, which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (15) or 2-(tetradecyl)hexadecan-1-ol (24), gave the lipophilic derivatives 16 and 25. Compound 16 was transformed, via selective reduction of the azido group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the title compound 18 in good yield. Compound 25 was treated with hydrazine acetate to give compound 26, which in turn was transformed, via sulfation or phosphorylation, and O-deacylation, into the target compounds 28 and 31.

  DOI：

  10.1080/07328309608005662