(+/-)-(1RS,3SR,4RS,5RS,6RS)-3-(hydroxymethyl)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-one | 139426-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1RS,3SR,4RS,5RS,6RS)-3-(hydroxymethyl)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-one
• 英文别名: (+/-)-(1RS,3SR,4RS,5RS,6RS)-3-(hydroxymethyl)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one
• CAS: 139426-56-5
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: ILCOHJWMDFDSEW-GXHGQEQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 7-oxabicyclo<2.2.1>hepta-2,3-diol-5-one, isopropyl acetal 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以40%的产率得到(+/-)-(1RS,3SR,4RS,5RS,6RS)-3-(hydroxymethyl)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-one
  参考文献：
  名称：

  Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (naked sugars) as synthetic intermediates. 18. Synthesis of .alpha.-(1.fwdarw.2)-, .alpha.-(1.fwdarw.3)-, .alpha.-(1.fwdarw.4)-, and .alpha.-(1.fwdarw.5)-C-linked disaccharides through 2,3,4,6-tetra-O-acetylglucopyranosyl radical additions to 3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one derivatives

  摘要：

  The ''naked sugar'' (+)-1 (1R,2S,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S')-camphanate) has been converted into (+)-(1R,4R,5R,6R)-3-methylidene-5-exo,6-exo(isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((+)-3) and (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one ((-)-26). Reductive addition of 2,3,4,6-tetra-O-acetylglucopyranosyl radical onto (+)-3 and (-)-26 were highly stereoselective giving exclusively 3-endo-(glucosylmethyl)-7-oxabicyclo[2.2.1]heptan-2-one derivatives. The anomeric selectivity (alpha-C-glucoside vs beta-C-glucoside) was 5.5:1 with (+)-3 and 8:1 with (-)-26. The C-glucosides so-obtained were transformed into alpha-(1 --> 2)-, alpha-(1 --> 3)-, alpha-(1 --> 4)-, and alpha-(1 --> 5)-C-linked disaccharide derivatives which combine alpha-D-glucopyranose with L-altro-hexonolactone, L-manno-hexonolactone, L-mannose, and L-(talo-hexofuranosid)uronic acid, respectively.

  DOI：

  10.1021/jo00033a032