allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-α-D-xylopyranoside | 1000385-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-α-D-xylopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)]Araf(a1-2)Xyl(a)-O-allyl；[(2S,3S,4R,5S)-3,4-dibenzoyloxy-5-[(2S,3R,4S,5R)-4,5-dihydroxy-2-prop-2-enoxyoxan-3-yl]oxyoxolan-2-yl]methyl benzoate
• CAS: 1000385-06-7
• 化学式: C₃₄H₃₄O₁₂
• 分子量: 634.637
• InChiKey: GQAKZBGMPNRYNJ-KHZVEEEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-α-D-xylopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以100%的产率得到
  参考文献：
  名称：

  Synthesis of a library of allyl α-l-arabinofuranosyl-α- or β-d-xylopyranosides; route to higher oligomers

  摘要：

  Six isomeric disaccharides allyl 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl-alpha-D-xylopyranosides and beta-D-xylopyranosides were synthetized by the stereoselective glycosylation of pure allyl alpha- or beta-D-xylopyranosides with 1-O-acetyl-2,3,5-tri-O-benzoyl-L-arabinofuranose as donor, catalyzed with BF3.Et2O in DCM. Regio- and stereoselective glycosylation with excess of donor furnished almost exclusively the trisaccharides allyl 2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-alpha- or beta-D-xylopyranosides. Extension of the reaction to the triol beta-D-xylopyranosyl-(1 -> 4)-1,2,3-tri-O-acetyl-alpha-D-xylopyranose, obtained from the 4-hydroxyl penta-O-acetyl-alpha-xylobiose, gave in the same manner the tetrasaccharide [2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D-xylopyranosyl]-(1 -> 4 )-1,2,3-tri-O-acetyl-alpha-D-xylopyranose. The protocol described herein should offer the possibility to produce branched oligosaccharides with a 2,3-di-O-(alpha-L-Ara(f))-beta-D-Xyl(p) block unit at the terminal non-reducing end. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.007
• 作为产物：
  描述：

  allyl α-D-xylopyranoside 、 1-O-acetyl-2,3,5-tri-O-benzoyl-α-L-arabinofuranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以377 mg的产率得到allyl 2,3-di-O-(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl)-α-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of a library of allyl α-l-arabinofuranosyl-α- or β-d-xylopyranosides; route to higher oligomers

  摘要：

  Six isomeric disaccharides allyl 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl-alpha-D-xylopyranosides and beta-D-xylopyranosides were synthetized by the stereoselective glycosylation of pure allyl alpha- or beta-D-xylopyranosides with 1-O-acetyl-2,3,5-tri-O-benzoyl-L-arabinofuranose as donor, catalyzed with BF3.Et2O in DCM. Regio- and stereoselective glycosylation with excess of donor furnished almost exclusively the trisaccharides allyl 2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-alpha- or beta-D-xylopyranosides. Extension of the reaction to the triol beta-D-xylopyranosyl-(1 -> 4)-1,2,3-tri-O-acetyl-alpha-D-xylopyranose, obtained from the 4-hydroxyl penta-O-acetyl-alpha-xylobiose, gave in the same manner the tetrasaccharide [2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D-xylopyranosyl]-(1 -> 4 )-1,2,3-tri-O-acetyl-alpha-D-xylopyranose. The protocol described herein should offer the possibility to produce branched oligosaccharides with a 2,3-di-O-(alpha-L-Ara(f))-beta-D-Xyl(p) block unit at the terminal non-reducing end. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.007

文献信息

• Synthesis of a library of allyl α-l-arabinofuranosyl-α- or β-d-xylopyranosides; route to higher oligomers
  作者：Jean-Pierre Utille、Isabelle Jeacomine

  DOI：10.1016/j.carres.2007.08.007

  日期：2007.12

  Six isomeric disaccharides allyl 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl-alpha-D-xylopyranosides and beta-D-xylopyranosides were synthetized by the stereoselective glycosylation of pure allyl alpha- or beta-D-xylopyranosides with 1-O-acetyl-2,3,5-tri-O-benzoyl-L-arabinofuranose as donor, catalyzed with BF3.Et2O in DCM. Regio- and stereoselective glycosylation with excess of donor furnished almost exclusively the trisaccharides allyl 2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-alpha- or beta-D-xylopyranosides. Extension of the reaction to the triol beta-D-xylopyranosyl-(1 -> 4)-1,2,3-tri-O-acetyl-alpha-D-xylopyranose, obtained from the 4-hydroxyl penta-O-acetyl-alpha-xylobiose, gave in the same manner the tetrasaccharide [2,3-di-O-(2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosyl)-beta-D-xylopyranosyl]-(1 -> 4 )-1,2,3-tri-O-acetyl-alpha-D-xylopyranose. The protocol described herein should offer the possibility to produce branched oligosaccharides with a 2,3-di-O-(alpha-L-Ara(f))-beta-D-Xyl(p) block unit at the terminal non-reducing end. (c) 2007 Elsevier Ltd. All rights reserved.