(2R,3R,4S,5S,6R)-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 | 1053262-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4S,5S,6R)-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
• 英文别名: (2R,3R,4S,5S,6R)-6-ethylsulfanyl-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]hexane-1,2,3,4,5-pentol
• CAS: 1053262-69-3
• 化学式: C₂₀H₃₆O₁₁S
• 分子量: 484.565
• InChiKey: RWSRCPGATFGLEM-CJZDQBCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  182
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4S,5S,6R)-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 在 4-二甲氨基吡啶 、 mercury dichloride 、 mercury(II) oxide 作用下， 生成 6-O-(2,3,5,6-tetra-O-acetyl-β-D-mannofuranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  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-mannose diethyl dithioacetal 在 molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 silver trifluoromethanesulfonate 、 乙酰氯 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2R,3R,4S,5S,6R)-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

文献信息

• Use of Acyclic Glycosyl Donors for Furanoside Synthesis
  作者：Joseph C. McAuliffe、Ole Hindsgaul

  DOI：10.1021/jo9618583

  日期：1997.3.1

  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.