4(S),5(R)-dihydroxy-4,6(R)-dimethyl-tetrahydro-pyran-2-one | 476468-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4(S),5(R)-dihydroxy-4,6(R)-dimethyl-tetrahydro-pyran-2-one
• 英文别名: (4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-one
• CAS: 476468-31-2
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: AZYUXMUKVNHLNC-QXRNQMCJSA-N

物化性质

• 沸点：
  306.7±42.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4(S),5(R)-dihydroxy-4,6(R)-dimethyl-tetrahydro-pyran-2-one 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 16.0h， 生成 2,4,6-trideoxy-3-methyl-β-D-ribo-hexopyranose 、 2,4,6-trideoxy-3-methyl-α-D-ribo-hexopyranose
  参考文献：
  名称：

  Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis

  摘要：

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.

  DOI：

  10.1021/ol026710m
• 作为产物：
  描述：

  3-甲基丁-3-烯酸 在 potassium dioxotetrahydroxoosmate(VI) titanium(IV) isopropylate 、 potassium dihydrogenphosphate 、 Hydroquinone 1,4-phthalazinediyl diether 、 对甲苯磺酸 、 potassium hexacyanoferrate(III) 作用下， 以 氯仿 、 水 、 叔丁醇 为溶剂， 反应 7.5h， 生成 4(S),5(R)-dihydroxy-4,6(R)-dimethyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis

  摘要：

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.

  DOI：

  10.1021/ol026710m

文献信息

• Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis
  作者：Peter R. Andreana、Jason S. McLellan、Yongchen Chen、Peng George Wang

  DOI：10.1021/ol026710m

  日期：2002.10.1

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.