methyl-(5-deoxy-2,3-O-isopropyliden-D-ribofuranoside) | 111904-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-(5-deoxy-2,3-O-isopropyliden-D-ribofuranoside)
• 英文别名: 1-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose
• CAS: 111904-82-6
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: HOFBZYYLBQZCHH-PILSHRGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl-(5-deoxy-2,3-O-isopropyliden-D-ribofuranoside) 在 盐酸 、 对甲苯磺酸 、 zinc dibromide 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 生成 (2S,3R,4S,5R)-2-Allyl-2,5-dimethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Chemistry of F1,F0-ATPase inhibitors. Stereoselective total syntheses of (+)-citreoviral and (-)-citreoviridin

  摘要：

  DOI：

  10.1021/ja00210a026
• 作为产物：
  描述：

  5-chloro-2,3-O-isopropylidene-D-ribono-1,4-lactone 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醚 为溶剂， 生成 methyl-(5-deoxy-2,3-O-isopropyliden-D-ribofuranoside)
  参考文献：
  名称：

  Chemistry of F1,F0-ATPase inhibitors. Stereoselective total syntheses of (+)-citreoviral and (-)-citreoviridin

  摘要：

  DOI：

  10.1021/ja00210a026

文献信息

• Osmium Catalyzed Dihydroxylation of 1,2-Dioxines:  A New Entry for Stereoselective Sugar Synthesis
  作者：Tony V. Robinson、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo060949p

  日期：2006.9.1

  A series of 3,6-substituted 3,6-dihydro-1,2-dioxines were dihydroxylated with osmium tetroxide to furnish 1,2-dioxane-4,5-diols (peroxy diols) in yields ranging from 33% to 98% and with de values not less than 90%. The peroxy diols were then reduced to generate a stereospecific tetraol core with R, R, S, S or "allitol" stereochemistry. The peroxy diols and their acetonide derivatives were also ring-opened with Co(II) salen complexes to give novel hydroxy ketones in 77-100% yield, including the natural sugar psicose. Importantly, preliminary work on the catalytic asymmetric ring-opening of meso-peroxy diols using the Co(II) Jacobsens's catalyst indicates that asymmetric sugar synthesis from 1,2-dioxines is possible.