1-deoxy-1-α-ethenyl-3,4,5-tri-O-benzyl-D-glucose | 294872-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-α-ethenyl-3,4,5-tri-O-benzyl-D-glucose
• 英文别名: (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)ethene；(2R,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-ol；(2α,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol；(2R,3S,4R,5R,6R)-2-ethenyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 294872-82-5
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: UFXIZCQEFAYYDJ-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-α-ethenyl-3,4,5-tri-O-benzyl-D-glucose 在 2,6-二甲基吡啶 、 四丁基碘化铵 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Synthesis of the C1-phosphonate analog of UDP-GlcNAc

  摘要：

  We describe the first synthesis of the Cl-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (K-i > 10 mM) of fungal chitin synthase, indicating that at least in this case the replacement of the anomeric oxygen with a methylene group is not an innocent substitution. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.05.008
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 trivinylaluminum 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 生成 1-deoxy-1-α-ethenyl-3,4,5-tri-O-benzyl-D-glucose
  参考文献：
  名称：

  Synthesis of the C1-phosphonate analog of UDP-GlcNAc

  摘要：

  We describe the first synthesis of the Cl-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (K-i > 10 mM) of fungal chitin synthase, indicating that at least in this case the replacement of the anomeric oxygen with a methylene group is not an innocent substitution. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.05.008

文献信息

• C-Glycosides to fused polycyclic ethers
  作者：Shawn P. Allwein、Jason M. Cox、Brett E. Howard、Henry W.B. Johnson、Jon D. Rainier

  DOI：10.1016/s0040-4020(02)00057-1

  日期：2002.3

  This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• From <i>α</i>‐1,2‐Anhydrosugars to <i>C</i>‐Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry
  作者：Michiel A. Leeuwenburgh、Gijsbert A. van der Marel、Herman S. Overkleeft、Jacques H. van Boom

  DOI：10.1081/car-120026458

  日期：2003.12.31

  Ring opening of the epoxide function in alpha-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford alpha-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation alpha/beta mixtures. Vinyl nucleophiles predominantly afford alpha-products, whereas allyl and allenyl species almost exclusively yield beta-C-glycosides.
• Cross-metathesis and ring-closing metathesis of olefinic monosaccharides
  作者：Maarten H.D. Postema、Jared L. Piper

  DOI：10.1016/s0040-4039(02)01617-9

  日期：2002.9

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Aluminum- and Boron-Mediated C-Glycoside Synthesis from 1,2-Anhydroglycosides
  作者：Jon D. Rainier、Jason M. Cox

  DOI：10.1021/ol006286u

  日期：2000.8.1

  [GRAPHICS]This letter describes a single flask strategy to the synthesis of a alpha-C-glycosides from glycals. This protocol couples a glycal epoxidation reaction with a C-2 alkoxy-directed carbon-carbon bond forming reaction.
• Highly stereoselective synthesis of C-vinyl pyranosides via a Pd0-mediated cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enitols
  作者：Ernest G. Nolen、Vivian C. Ezeh、Matthew J. Feeney

  DOI：10.1016/j.carres.2014.07.002

  日期：2014.9

  Oct-2-enitols undergo a Pd(0)-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical preference during cyclization, the α- and β-epimeric ratios are enhanced by double diastereoselection using the (S,S) or (R,R)-DACH ligands.