1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone | 263544-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone
• 英文别名: 1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanone
• CAS: 263544-57-6
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: YKKQMRWBZMTVHG-BYNSBNAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone 在 4-二甲氨基吡啶 、 sodium periodate 、 乙醇 、 硫酸 、 L-Selectride 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 生成 2,2-Dimethyl-propionic acid (E)-(1S,2R)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-{(R)-4-[1-methoxy-meth-(E)-ylidene]-2-methyl-3-oxo-tetrahydro-furan-2-yl}-hexa-3,5-dienyl ester
  参考文献：
  名称：

  An approach to quassimarin based on an exo-selective intramolecular Diels-Alder reaction

  摘要：

  DOI：

  10.1021/jo00220a064
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-6-Benzyloxy-5-(2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 在 sodium t-butanolate 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone
  参考文献：
  名称：

  Reaction of 5,6-cyclic sulfates derived from glycofuranoses with bases. A one-pot synthesis of 6-deoxy-hexofuranos-5-ulose derivatives

  摘要：

  Methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside 1 reacted with nitrogen bases to give the corresponding aminosulfates. Strong bases such as sodium tert-butoxide or n-butyllithium afforded methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexanofuranos-5-uloside 7. The reaction was optimized with sodium tert-butoxide and applied to three other 5,6-cyclic sulfates derived from aldofuranosides to give the corresponding keto-aldoses in good yields. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02158-9

文献信息

• Reaction of 5,6-cyclic sulfates derived from glycofuranoses with bases. A one-pot synthesis of 6-deoxy-hexofuranos-5-ulose derivatives
  作者：Thierry Gourlain、Anne Wadouachi、Daniel Beaupère

  DOI：10.1016/s0040-4039(99)02158-9

  日期：2000.1

  Methyl 2,3-O-isopropylidene-5,6-O-sulfuryl-alpha-D-mannofuranoside 1 reacted with nitrogen bases to give the corresponding aminosulfates. Strong bases such as sodium tert-butoxide or n-butyllithium afforded methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexanofuranos-5-uloside 7. The reaction was optimized with sodium tert-butoxide and applied to three other 5,6-cyclic sulfates derived from aldofuranosides to give the corresponding keto-aldoses in good yields. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.
• An approach to quassimarin based on an exo-selective intramolecular Diels-Alder reaction
  作者：R. H. Schlessinger、J. W. Wong、M. A. Poss、James P. Springer

  DOI：10.1021/jo00220a064

  日期：1985.10