2-C-methyl-D-erythrofuranose | 258518-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-C-methyl-D-erythrofuranose
• 英文别名: 2-C-(methyl)-D-erythrose；(3R,4R)-3-methyloxolane-2,3,4-triol
• CAS: 258518-32-0
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: CIZLDZCLFUFYMS-MCZAYYIJSA-N

物化性质

• 沸点：
  268.0±40.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 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

• 作为反应物：
  描述：

  2-C-methyl-D-erythrofuranose 在 molybdenum(VI) oxide 作用下， 以 水 为溶剂， 反应 0.67h， 以95%的产率得到1-脱氧-D-木酮糖
  参考文献：
  名称：

  1-Deoxy-d-xylulose:  Synthesis Based on Molybdate-Catalyzed Rearrangement of a Branched-Chain Aldotetrose

  摘要：

  [GRAPHICS]1-Deoxy-D-xylulose has been prepared in seven steps and similar to 21% overall yield from 2,3-O-isopropylidene-D-erythrono-1,4-lactone. The key reaction involves transformation of a branched-chain aldotetrose to the 1-deoxy-2-ketopentose catalyzed by molybdic acid. Other branched-chain aldotetroses containing bulkier substituents at C2 also engage in the conversion, suggesting routes to protected 2-ketoses and alpha -ketoacids/ esters. This synthetic route mimics reactions of the non-mevalonate isoprenoid pathway in plants and bacteria.

  DOI：

  10.1021/ol016265f
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-2-C-(hydroxymethyl)-β-D-erythrofuranoside 在 吡啶 、 lithium aluminium tetrahydride 、 Dowex HCR-W₂ (H⁺) 作用下， 以 甲醇 、 乙醚 、 氯仿 、 水 为溶剂， 反应 33.0h， 生成 2-C-methyl-D-erythrofuranose
  参考文献：
  名称：

  1-Deoxy-d-xylulose:  Synthesis Based on Molybdate-Catalyzed Rearrangement of a Branched-Chain Aldotetrose

  摘要：

  [GRAPHICS]1-Deoxy-D-xylulose has been prepared in seven steps and similar to 21% overall yield from 2,3-O-isopropylidene-D-erythrono-1,4-lactone. The key reaction involves transformation of a branched-chain aldotetrose to the 1-deoxy-2-ketopentose catalyzed by molybdic acid. Other branched-chain aldotetroses containing bulkier substituents at C2 also engage in the conversion, suggesting routes to protected 2-ketoses and alpha -ketoacids/ esters. This synthetic route mimics reactions of the non-mevalonate isoprenoid pathway in plants and bacteria.

  DOI：

  10.1021/ol016265f

文献信息

• An Efficient Preparation of 2-<i>C</i>-Methyl-<scp>d</scp>-Erythritol 4-Phosphoric Acid and Its Derivatives
  作者：Klaus Kis、Juraithip Wungsintaweekul、Wolfgang Eisenreich、Meinhart H. Zenk、Adelbert Bacher

  DOI：10.1021/jo9905118

  日期：2000.1.1
• Dihydroxylation of 4-Substituted 1,2-Dioxines: A Concise Route to Branched Erythro Sugars
  作者：Tony V. Robinson、Daniel Sejer Pedersen、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo900669u

  日期：2009.7.17

  The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.