methyl 2,3-O-isopropylidene 2-C-(methyl)-β-D-erythrofuranoside | 396092-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-isopropylidene 2-C-(methyl)-β-D-erythrofuranoside
• CAS: 396092-71-0
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: UJRBCHVUJRLHIK-ZXFLCMHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-isopropylidene 2-C-(methyl)-β-D-erythrofuranoside 在 Dowex HCR-W₂ (H⁺) 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以92%的产率得到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
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-2-C-(hydroxymethyl)-β-D-erythrofuranoside 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 32.0h， 生成 methyl 2,3-O-isopropylidene 2-C-(methyl)-β-D-erythrofuranoside
  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