methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside | 851367-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside
• 英文别名: Methyl 2,3,5-tri-O-acetyl-L-arabinofuranoside；[(2S,3S,4R)-3,4-diacetyloxy-5-methoxyoxolan-2-yl]methyl acetate
• CAS: 851367-08-3
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: RUSRQHXGPHZZNI-WSMDXJOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside 在 咪唑 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氨 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Yin; Zhang; Zhang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 1, p. 90 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  L-arabinose 在 吡啶 、 硫酸 作用下， 生成 methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside
  参考文献：
  名称：

  Yin; Zhang; Zhang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 1, p. 90 - 94

  摘要：

  DOI：

文献信息

• Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases
  作者：Andrea Bordoni、Rosa M. de Lederkremer、Carla Marino

  DOI：10.1016/j.bmc.2010.05.038

  日期：2010.7

  Derivatives of 5-deoxy-beta-D-galactofuranose (5-deoxy-alpha-L-arabino-hexofuranose) have been synthesized starting from D-galacturonic acid. The synthesis of methyl 5-deoxy-alpha-L-arabino-hexofuranoside (14 alpha) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14 alpha was converted into per-O-acetyl-5-deoxy-alpha,beta-L-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19 alpha), and 4-methylthiophenyl 5-deoxy-alpha-L-arabino-hexofuranosides (20 alpha). The oxygenated analog 4-methylphenyl 1-thio-beta-D-galactofuranoside (23 beta) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-beta-D-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of a Dimer of β-(1,4)-<scp>l</scp>-Arabinosyl-(2<i>S</i>,4<i>R</i>)-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort
  作者：Ning Xie、Carol M. Taylor

  DOI：10.1021/ol102112z

  日期：2010.11.5

  N alpha-tert-Butoxycarbonyl-L-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAII) was glycosylated with 2,3,5-tri-O-benzyl-L-arabinose p-cresylthioglycoside in 60% yield with 4:1 beta:alpha stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.
• [EN] [4-(4-CYANOBENZOYL)PHENYL]GLYCOFURANOSIDE DERIVATIVES, USE OF SAID DERIVATIVES AS A MEDICAMENT, PRODUCTION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] DERIVES DE [4-(4-CYANOBENZOYL)PHENYL]GLYCOFURANOSIDE, UTILISATION EN TANT QUE MEDICAMENT, PROCEDE D'OBTENTION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：FOURNIER LAB SA

  公开号：WO2003002586A1

  公开（公告）日：2003-01-09

  La présente invention concerne de nouveaux derivés de [4-(4-cyanobenzoyl)phényl] glycofuranoside, de formule (I), dans laquelle R représente un groupe glycofuranosyle. Ces composés ont une activité anti-antiathéromateuse.
• Yin; Zhang; Zhang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 1, p. 90 - 94
  作者：Yin、Zhang、Zhang、Tang、Zhao

  DOI：——

  日期：——