methyl S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-4-thio-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-4-thio-α-D-glucopyranoside | 140484-35-1

• 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: methyl S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-4-thio-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-4-thio-α-D-glucopyranoside
• CAS: 140484-35-1
• 化学式: C₃₉H₅₄O₂₄S₂
• 分子量: 970.975
• InChiKey: SLFMVGWAZPFCKX-SGITXVJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  65.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  299.92
• 氢给体数：
  0.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  methyl S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-4-thio-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-4-thio-α-D-glucopyranoside 在 硫酸 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography

  摘要：

  4-Aminophenyl 1,4-dithio-beta-cellobioside (6) was obtained by treatment of methyl 2,3,6-tri-O-benzoyl-4-O-triflyl-alpha-D-galactopyranoside with the sodium salt of 1-thio-beta-D-glucopyranose, followed by acetolysis and glycosylation of the corresponding bromide with 4-aminobenzenethiol and subsequent deacylation. A similar synthesis starting with the 1-thiolate of 1,4-dithio-beta-cellobiose led to the trisaccharide 4-aminophenyl 1,4,4'-trithiocellotrioside (16). The 4-acetamidophenyl di- and tri-thiocellooligosaccharides were found to be excellent competitive inhibitors of the hydrolysis of 4-methylumbelliferyl beta-lactoside with respective K(i) values of 25 and 6.5mM. The two 4-aminophenyl oligosaccharides 6 and 16 were coupled to CH-Sepharose 4B, and the affinity gels were used for the purification of cellobiohydrolases from a crude commercial cellulolytic extract of T. reesei. Cellobiohydrolases I or II were selectively desorbed from gels bearing ligands 6 and 16.

  DOI：

  10.1016/0008-6215(92)84090-f
• 作为产物：
  描述：

  乙酸酐 、 (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylsulfanyl)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-ylsulfanyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 作用下， 生成 methyl S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-4-thio-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-4-thio-α-D-glucopyranoside
  参考文献：
  名称：

  4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography

  摘要：

  4-Aminophenyl 1,4-dithio-beta-cellobioside (6) was obtained by treatment of methyl 2,3,6-tri-O-benzoyl-4-O-triflyl-alpha-D-galactopyranoside with the sodium salt of 1-thio-beta-D-glucopyranose, followed by acetolysis and glycosylation of the corresponding bromide with 4-aminobenzenethiol and subsequent deacylation. A similar synthesis starting with the 1-thiolate of 1,4-dithio-beta-cellobiose led to the trisaccharide 4-aminophenyl 1,4,4'-trithiocellotrioside (16). The 4-acetamidophenyl di- and tri-thiocellooligosaccharides were found to be excellent competitive inhibitors of the hydrolysis of 4-methylumbelliferyl beta-lactoside with respective K(i) values of 25 and 6.5mM. The two 4-aminophenyl oligosaccharides 6 and 16 were coupled to CH-Sepharose 4B, and the affinity gels were used for the purification of cellobiohydrolases from a crude commercial cellulolytic extract of T. reesei. Cellobiohydrolases I or II were selectively desorbed from gels bearing ligands 6 and 16.

  DOI：

  10.1016/0008-6215(92)84090-f