3-O-acetyl-5-S-acetyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose | 190599-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-5-S-acetyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose
• 英文别名: [(3aR,5S,6R,6aR)-5-[(1S)-1-acetylsulfanylethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 190599-24-7
• 化学式: C₁₃H₂₀O₆S
• 分子量: 304.364
• InChiKey: FMCQXCJZHQCTMR-MWAPLWLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-5-S-acetyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose 在 sodium methylate 、 溶剂黄146 作用下， 生成 (2R,3R,4S,5S,6S)-6-methylthiane-2,3,4,5-tetrol 、 (2S,3R,4S,5S,6S)-6-methylthiane-2,3,4,5-tetrol
  参考文献：
  名称：

  Applications of Cyclic Sulfates of vic-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars

  摘要：

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

  DOI：

  10.1021/jo962066b
• 作为产物：
  描述：

  1,2-o-异亚丙基-alpha-d-呋喃葡萄糖-3-乙酸酯 在 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 3.0h， 生成 3-O-acetyl-5-S-acetyl-6-deoxy-1,2-O-isopropylidene-5-thio-β-L-idofuranose
  参考文献：
  名称：

  Applications of Cyclic Sulfates of vic-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars

  摘要：

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

  DOI：

  10.1021/jo962066b