4(R),5(S)-dihydroxy-4,6(S)-dimethyl-tetrahydro-pyran-2-one | 67470-68-2

• 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(R),5(S)-dihydroxy-4,6(S)-dimethyl-tetrahydro-pyran-2-one
• 英文别名: 3-methyl-L-ribo-2,6-dideoxy-hexonic acid-5-lactone；3-Methyl-L-ribo-2,6-didesoxy-hexonsaeure-5-lacton；(4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-one
• CAS: 67470-68-2
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: AZYUXMUKVNHLNC-JSKYLQRQSA-N

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(R),5(S)-dihydroxy-4,6(S)-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 β-L-mycarose 、 α-L-mycarose
  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 RuCl₂(=CHPh)(PCy₃)(1,3-Mes-2-imidazolidin-2-yl) 、 K₂OsOs(OH)4 titanium(IV) isopropylate 、 potassium dihydrogenphosphate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 氯仿 、 水 、 叔丁醇 为溶剂， 反应 7.5h， 生成 4(R),5(S)-dihydroxy-4,6(S)-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

• MAGNAMYCIN.¹ II. MYCAROSE, AN UNUSUAL BRANCHED-CHAIN DESOXYSUGAR FROM MAGNAMYCIN
  作者：P. P. Regna、F. A. Hochstein、R. L. Wagner、R. B. Woodward

  DOI：10.1021/ja01114a542

  日期：1953.9
• 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.