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 | 143571-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 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
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-5-hydroxy-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 143571-63-5
• 化学式: C₇₄H₈₉NO₁₅Si
• 分子量: 1260.6
• InChiKey: AFBOWOCVWAZOAR-JDNGPKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.53
• 重原子数：
  91.0
• 可旋转键数：
  32.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  169.32
• 氢给体数：
  2.0
• 氢受体数：
  15.0

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 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-1-thio-β-D-galactopyranoside 在 4 A molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 84.0h， 以46%的产率得到2-(Trimethylsilyl)ethyl O-(2-O-benzoyl-4,6-O-benzylidene-3-O-levulinoyl-β-D-galactopyranosyl)-(1->4)-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-galacto...
  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：

  [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate 在 盐酸 、 sodium cyanoborohydride 、 对甲苯磺酸 、 一水合肼 、 DMTST 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 12.0h， 生成 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
  参考文献：
  名称：

  立体控制合成唾液酸化的Lewis X神经酰胺，其由选择素家族识别的五糖组成。

  摘要：

  DOI：

  10.1016/s0008-6215(00)90524-x

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。