methyl 2,3-O-isopropylidene-2-C-(hydroxymethyl)-β-D-erythrofuranoside | 396092-69-6

• 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-(hydroxymethyl)-β-D-erythrofuranoside
• 英文别名: [(3aR,4R,6aR)-4-methoxy-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-3a-yl]methanol
• CAS: 396092-69-6
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: KJNIEXSPFHSSQH-ZXFLCMHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  D-erythronolactone acetonide 在 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 为溶剂， 反应 121.5h， 生成 methyl 2,3-O-isopropylidene-2-C-(hydroxymethyl)-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

文献信息

• 1-Deoxy-<scp>d</scp>-xylulose:  Synthesis Based on Molybdate-Catalyzed Rearrangement of a Branched-Chain Aldotetrose
  作者：Shikai Zhao、Ladislav Petrus、Anthony S. Serianni

  DOI：10.1021/ol016265f

  日期：2001.11.1

  [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.