1,2:3,4-di-O-isopropylidene-6-O-vinyl-α-D-galactopyranose | 105618-01-7

• 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: 1,2:3,4-di-O-isopropylidene-6-O-vinyl-α-D-galactopyranose
• 英文别名: (1S,2R,6R,8R,9S)-8-(ethenoxymethyl)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 105618-01-7
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: CFMSYOCRTVVRPG-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 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 、 1,2:3,4-di-O-isopropylidene-6-O-vinyl-α-D-galactopyranose 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以86%的产率得到(5RS)-5-[6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyloxy)]-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：

  1,2:3,4-di-O-isopropylidene-6-O-[(E)-2'-(phenylsulfonyl)vinyl]-α-D-galactopyranose 在 sodium dihydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 为溶剂， 以66%的产率得到1,2:3,4-di-O-isopropylidene-6-O-vinyl-α-D-galactopyranose
  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。
• 1-<i>O</i>-Vinyl Glycosides via Tebbe Olefination, Their Use as Chiral Auxiliaries and Monomers
  作者：Jialong Yuan、Kristof Lindner、Holger Frauenrath

  DOI：10.1021/jo0600510

  日期：2006.7.1

  perspective to use the 1-O-vinyl glycosides as monomers for the preparation of glycosylated poly(vinyl alcohol) derivatives with controlled tacticity, their scope as chiral auxiliaries for a stereodifferentiation in addition reactions to the olefin function was investigated by using the [2+2] cycloaddition to dichloroketene as a model reaction. In particular, vinyl 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranoside

  制备了一系列的端基纯的1- O-甲酰基糖苷1，并通过Tebbe烯化将其转化为相应的1- O-乙烯基糖苷2。以良好的收率获得了未取代的乙烯基糖苷，为异构体纯的化合物，其制备方法与多种官能团的存在相容。显着地，在乙酸盐和苯甲酸酯保护基的存在下，将异头甲酸酯基区域选择性地转化为相应的烯烃。用角度来看要用1- O-乙烯基糖苷作为单体，用于制备具有可控制的立构规整度的糖基化聚乙烯醇衍生物，通过使用[2 + 2]环化成二氯乙烯酮的方法研究了它们作为立体分化的手性助剂的范围以及对烯烃功能的加成反应。模型反应。特别地，乙烯基2,3,4,6-四-O-苯甲酰基-α - d-甘露吡喃糖苷（2i）表现出优异的非对映选择性。最后，1- ø -乙烯基苷成功经受大量的自由基均聚或用作与马来酸酐自由基共聚得到交替富电子的共聚单体，糖基化的聚（乙烯醇- ALT -马来酸酐）。
• 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.
• Palladium(II)-Catalyzed Transfer Vinylation of Protected Monosaccharides
  作者：Sean Handerson、Marcel Schlaf

  DOI：10.1021/ol017104e

  日期：2002.2.1

  A method for the catalytic vinylation of protected monosaccharides bearing a single free hydroxyl function has been developed. Reaction of representative primary, secondary, and anomeric sugar hydroxyl functions with butyl vinyl ether as the reactant and solvent and (phen)Pd-(OAc)(2) (phen = 1,10-phenanthroline ligand) as the catalyst gives the corresponding vinylated sugar products in 36-79% yield. The catalyst requires the presence of traces of oxygen in the reaction mixture to prevent decomposition to Pd(0).
• 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.