Acetic acid (1R,2S,3R,4R)-2,3,4,5-tetraacetoxy-1-[(S)-ethylsulfanyl-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-methyl]-pentyl ester | 187842-85-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: Acetic acid (1R,2S,3R,4R)-2,3,4,5-tetraacetoxy-1-[(S)-ethylsulfanyl-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-methyl]-pentyl ester
• CAS: 187842-85-9
• 化学式: C₃₀H₄₆O₁₆S
• 分子量: 694.752
• InChiKey: JCOCZSCQHMGFHM-HPVROLARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 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,3R,4R)-2,3,4,5-tetraacetoxy-1-[(S)-ethylsulfanyl-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-methyl]-pentyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5R,6S)-6-Ethylsulfanyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-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：

  Acetic acid (1S,2R,3R)-2,3,4-triacetoxy-1-((R)-1-acetoxy-2-chloro-2-ethylsulfanyl-ethyl)-butyl ester 、 双丙酮半乳糖 在 molecular sieve 、 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到Acetic acid (1R,2S,3R,4R)-2,3,4,5-tetraacetoxy-1-[(S)-ethylsulfanyl-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-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