(S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-yn-1-ol | 188640-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-yn-1-ol
• CAS: 188640-81-5
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: ZKADUCHYHHRNQB-VPJKUYQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-yn-1-ol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 silver(I) acetate 作用下， 以 丙酮 为溶剂， 生成 Acetic acid (S)-4-bromo-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-ynyl ester
  参考文献：
  名称：

  Diastereoselective propargylation of sugar aldehydes. New synthesis of 6-deoxyheptoses

  摘要：

  Propargylation of pentofuranose aldehydes by treatment with propargyl bromide in the presence of zinc dust yielded homopropargylic alcohols with a good isolated yield and, in many cases, excellent anti/syn selectivity. Catalytic hydrogenation of the triple bond afforded homoallylic alcohols, valuable substrates for the synthesis of 6-deoxyheptoses. Direct ozonolysis of the triple bond yielded uronic acid esters. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01156-8
• 作为产物：
  描述：

  (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 、 3-溴丙炔 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以11%的产率得到(S)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-yn-1-ol
  参考文献：
  名称：

  Diastereoselective propargylation of sugar aldehydes. New synthesis of 6-deoxyheptoses

  摘要：

  Propargylation of pentofuranose aldehydes by treatment with propargyl bromide in the presence of zinc dust yielded homopropargylic alcohols with a good isolated yield and, in many cases, excellent anti/syn selectivity. Catalytic hydrogenation of the triple bond afforded homoallylic alcohols, valuable substrates for the synthesis of 6-deoxyheptoses. Direct ozonolysis of the triple bond yielded uronic acid esters. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01156-8