1,2:4,5-di-O-isopropylidene-3-O-vinyl-β-D-fructopyranose | 512198-36-6

• 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-fructopyranose
• 英文别名: (3'aR,4S,7'S,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: 512198-36-6
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: ZKDFTVBOMDXWHJ-PUHVVEEASA-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-fructopyranose 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-fructopyranosyloxy)]-3-phenyl-4,5-dihydroisoxazole 、 (5S)-5-[3-(1,2:4,5-di-O-isopropylidene-β-D-fructopyranosyloxy)]-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：

  1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 在 sodium dihydrogenphosphate 、 sodium amalgam 、 四丁基溴化铵 、 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-fructopyranose
  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

• A Green and Sustainable Route to Carbohydrate Vinyl Ethers for Accessing Bioinspired Materials with a Unique Microspherical Morphology
  作者：Konstantin S. Rodygin、Irina Werner、Valentine P. Ananikov

  DOI：10.1002/cssc.201701489

  日期：2018.1.10

  and biologically compatible. A green procedure has been developed for the vinylation of carbohydrates by using readily available calcium carbide. Various carbohydrates were utilized as starting materials, resulting in mono‐, di‐, and tetravinyl ethers in high to excellent yields (81–92 %). The synthesized biobased vinyl ethers were utilized as monomers in free radical and cationic polymerizations. A

  从可再生资源合成化学物质和材料是现代科学的主要目标之一。碳水化合物代表了极好的可再生天然原料，具有生态友好性，廉价和生物相容性。通过使用现成的电石，已经开发了一种绿色方法，用于碳水化合物的乙烯基化。各种碳水化合物被用作原料，以高到极好的收率（81–92％）产生单，二和四乙烯基醚。合成的生物基乙烯基醚被用作自由基和阳离子聚合反应的单体。在合成材料中实现了光滑表面和固有微隔室的独特组合。制备了两种类型的生物基材料，其中包括微球和聚合物中的固有中空隔室。
• Optimized Synthesis of Vinyl Ether Sugars and Vinyl Glycosides through Transfer Vinylation Catalyzed by (4,7‐Ph₂‐phen)Pd(OOCCF₃)₂
  作者：Martin Bosch、Sean Handerson、Marcel Schlaf

  DOI：10.1080/07328300802030852

  日期：2008.5

  Sugar vinyl ethers and vinyl glycosides are conveniently synthesized by catalytic transfer vinylation with butyl vinyl ether, which serves as both the solvent and source of vinyl. The air-stable catalyst (4,7-diphenyl-1,10-phenanthroline)Pd(OOCCF(3))(2) is prepared in situ from commercially available components.
• 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.