Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester | 176690-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester
• CAS: 176690-60-1
• 化学式: C₂₆H₃₅BrO₁₆S
• 分子量: 715.524
• InChiKey: HWYFHCXDBJZHKP-ZXTHBUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  202.56
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester 在 吡啶 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-diacetylamino-phenylsulfanyl)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester
  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：

  1,2,3,6-tetra-O-acetyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-α-D-glucopyranose 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester
  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

文献信息

• Enzymic synthesis of hemithiocellodextrins
  作者：Vincent Moreau、Hugues Driguez

  DOI：10.1039/p19960000525

  日期：——

  A commercial cellulase mixture was used for the enzymic oligomerisation of 4-thio-β-cellobiosyl fluoride 4 in a buffer/organic solvent system and led to the formation of water-soluble hemithiocellodextrins 6–10 with DP 4–14.

  在缓冲液/有机溶剂体系中，使用一种商业纤维素酶混合物对4-硫代-β-纤维二糖氟化物4进行酶促低聚反应，生成DP为4-14的水溶性半硫纤维素糊精6-10。