Acetic acid (1R,2S,3S,4R)-2,3,4,5-tetraacetoxy-1-[(S)-((2R,4aR,6S,7S,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-ethylsulfanyl-methyl]-pentyl ester | 187842-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1R,2S,3S,4R)-2,3,4,5-tetraacetoxy-1-[(S)-((2R,4aR,6S,7S,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-ethylsulfanyl-methyl]-pentyl ester
• CAS: 187842-88-2
• 化学式: C₃₉H₅₀O₁₆S
• 分子量: 806.882
• InChiKey: RPTRUEFYMRTDHO-VSDSUPHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  56.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  186.88
• 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 (1R,2S,3S,4R)-2,3,4,5-tetraacetoxy-1-[(S)-((2R,4aR,6S,7S,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-ethylsulfanyl-methyl]-pentyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2R,3S,4S,5R,6S)-6-((2R,4aR,6S,7S,8S,8aR)-7-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-ethylsulfanyl-hexane-1,2,3,4,5-pentaol
  参考文献：
  名称：

  Use of Acyclic Glycosyl Donors for Furanoside Synthesis

  摘要：

  Treatment of the peracetylated ethyl dithioacetals of D-glucose, D-galactose, and D-mannose with acetyl chloride and boron trifluoride diethyl etherate at reflux yields the known acyclic 1-chlorol-(ethylthio) derivatives. These compounds are shown to effectively glycosylate a variety of carbohydrate accepters using silver trifluoromethanesulfonate as the promotor, affording stereospecifically the corresponding acyclic O,S-acetals in good to excellent yield. Furthermore, following deacetylation, treatment of these O,S-acetals with a mixture of mercuric salts in either methanol or dimethylformamide gives rise to disaccharides terminating in D-furanosyl residues.

  DOI：

  10.1021/jo9618583
• 作为产物：
  描述：

  2,3,4,5,6-penta-O-acetyl-D-galactose diethyl dithioacetal 在 molecular sieve 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 、 乙酰氯 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 Acetic acid (1R,2S,3S,4R)-2,3,4,5-tetraacetoxy-1-[(S)-((2R,4aR,6S,7S,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-ethylsulfanyl-methyl]-pentyl ester
  参考文献：
  名称：

  Use of Acyclic Glycosyl Donors for Furanoside Synthesis

  摘要：

  Treatment of the peracetylated ethyl dithioacetals of D-glucose, D-galactose, and D-mannose with acetyl chloride and boron trifluoride diethyl etherate at reflux yields the known acyclic 1-chlorol-(ethylthio) derivatives. These compounds are shown to effectively glycosylate a variety of carbohydrate accepters using silver trifluoromethanesulfonate as the promotor, affording stereospecifically the corresponding acyclic O,S-acetals in good to excellent yield. Furthermore, following deacetylation, treatment of these O,S-acetals with a mixture of mercuric salts in either methanol or dimethylformamide gives rise to disaccharides terminating in D-furanosyl residues.

  DOI：

  10.1021/jo9618583