1,2:4,5-di-O-isopropylidene-3-O-vinyl-β-D-psicopyranose | 512198-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2:4,5-di-O-isopropylidene-3-O-vinyl-β-D-psicopyranose
• 英文别名: (3'aR,4S,7'R,7'aR)-7'-ethenoxy-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]
• CAS: 512198-37-7
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: ZKDFTVBOMDXWHJ-BIAAXOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲腈 N-氧化物 、 1,2:4,5-di-O-isopropylidene-3-O-vinyl-β-D-psicopyranose 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 (5R)-5-[3-(1,2:4,5-di-O-isopropylidene-β-D-psicopyranosyloxy)]-3-phenyl-4,5-dihydroisoxazole 、 (5S)-5-[3-(1,2:4,5-di-O-isopropylidene-β-D-psicopyranosyloxy)]-3-phenyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Sugar-based ethenyl ethers: stereoselective dipolar cycloadditions of nitrile oxides

  摘要：

  Selected sugar-based ethenyl ethers have been employed in 1,3-dipolar cycloaddition with nitrite oxides. In the D-fructo series, high diastercoselectivity was observed as compared with the 3-epimeriC D-psico series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00709-7
• 作为产物：
  描述：

  2,2,2',2'-四甲基四氢螺[1,3-二氧戊环-4,6'-[1,3]二氧杂环戊并[4,5-c]吡喃]-7'-醇 在 sodium dihydrogenphosphate 、 四丁基溴化铵 、 magnesium 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 1,2:4,5-di-O-isopropylidene-3-O-vinyl-β-D-psicopyranose
  参考文献：
  名称：

  Synthesis of sugar-based ethenyl ethers through a vinyl bis-sulfone methodology

  摘要：

  The recently devised route to ethenyl ethers-i.e. 1,2-bis(phenylsulfonyl)ethylene (BPSE)-mediated conversion of alcohols into beta-alkoxyvinyl sulfones followed by reductive desulfonylation-has been applied in the carbohydrate field to the synthesis of a number of vinyl-functionalised monosaccharides, a number of which had not been prepared via alternative routes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00661-6

文献信息

• Sugar-based ethenyl ethers: stereoselective dipolar cycloadditions of nitrile oxides
  作者：Matthieu Desroses、Florence Chéry、Arnaud Tatibouët、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/s0957-4166(02)00709-7

  日期：2002.11

  Selected sugar-based ethenyl ethers have been employed in 1,3-dipolar cycloaddition with nitrite oxides. In the D-fructo series, high diastercoselectivity was observed as compared with the 3-epimeriC D-psico series. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of sugar-based ethenyl ethers through a vinyl bis-sulfone methodology
  作者：Florence Chéry、Matthieu Desroses、Arnaud Tatibouët、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/s0040-4020(03)00661-6

  日期：2003.6

  The recently devised route to ethenyl ethers-i.e. 1,2-bis(phenylsulfonyl)ethylene (BPSE)-mediated conversion of alcohols into beta-alkoxyvinyl sulfones followed by reductive desulfonylation-has been applied in the carbohydrate field to the synthesis of a number of vinyl-functionalised monosaccharides, a number of which had not been prepared via alternative routes. (C) 2003 Elsevier Science Ltd. All rights reserved.