2,4,6-trideoxy-3-methyl-α-D-ribo-hexopyranose | 18423-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-trideoxy-3-methyl-α-D-ribo-hexopyranose
• 英文别名: L-Mycarose；3-methyl-D-ribo-2,6-dideoxy-hexose；3-methyl-α-D-ribo-2,6-dideoxy-hexopyranose；Mycarose alpha-D-pyranose；(2S,4S,5R,6R)-4,6-dimethyloxane-2,4,5-triol
• CAS: 18423-82-0；20108-38-7；26391-83-3；98168-04-8；98168-07-1；98168-10-6；98168-11-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: YQLFLCVNXSPEKQ-UCROKIRRSA-N

物化性质

• 沸点：
  308.1±42.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基丁-3-烯酸 在 potassium dioxotetrahydroxoosmate(VI) 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 23.5h， 生成 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

文献信息

• Substrate Flexibility of Vicenisaminyltransferase VinC Involved in the Biosynthesis of Vicenistatin
  作者：Atsushi Minami、Tadashi Eguchi

  DOI：10.1021/ja0685250

  日期：2007.4.1

  A glycosyltransferase VinC is involved in the biosynthesis of antitumor beta-glycoside antibiotic vicenistatin. It catalyzes a glycosyl transfer reaction between dTDP-alpha-D-vicenisamine and vicenilactam. Previous identification of its broad substrate specificity toward various glycosyl acceptors enabled us to explore the potential of VinC for glycodiversification. In vitro study of the substrate specificity toward several dTDP-sugars with vicenilactam established that VinC displayed activities with alpha-anomers of several dTDP-2-deoxy-D-sugars such as mycarose, digitoxose, olivose, and 2-deoxyglucose to afford respective beta-glycosides. Notably, beta-anomers of dTDP-2-deoxy-D-sugars also appeared to be accepted by VinC to form alpha-glycosides. Furthermore, VinC is capable of catalyzing glycosyl transfer reactions from both the alpha-anomer and beta-anomer of dTDP-L-mycarose, respectively, into beta-glycoside and alpha-glycoside. These results indicate that VinC is a unique glycosyltransferase possessing broad substrate specificity. The mechanism of this axially oriented glycosidic bond formation from the equatorially oriented dTDP-sugar might be explained by conformational change of dTDP-sugar to a boat conformation during the glycosyl transfer reaction. To apply these features of VinC for glycodiversification, 22 sets of structurally diverse glycosides were constructed using unnatural glycosyl donors and acceptors.
• 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.