2-C-(benzyloxymethyl)-D-erythrose | 396092-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-C-(benzyloxymethyl)-D-erythrose
• 英文别名: (3R,4R)-3-(phenylmethoxymethyl)oxolane-2,3,4-triol
• CAS: 396092-73-2
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: FAIJPXZFSWRJDC-IGBJHFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-C-(benzyloxymethyl)-D-erythrose 在 molybdenum(VI) oxide 作用下， 以 水 为溶剂， 反应 3.0h， 以62%的产率得到1-O-benzyl-D-xylulose
  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 氢氧化钾 、 硫酸 作用下， 反应 15.0h， 生成 2-C-(benzyloxymethyl)-D-erythrose
  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.