2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1-> 6)-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 249511-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1-> 6)-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: [(2S,3S,4R,5R)-5-[[(3aS,4R,6R,7R,7aR)-7-hydroxy-2,2-dimethyl-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy]-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 249511-76-0
• 化学式: C₄₇H₅₄O₁₈
• 分子量: 906.935
• InChiKey: PLSOWNRLRYULQL-YPRWJORFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  65
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  201
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1-> 6)-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2′-O-, 6′-O- and 2′,6′-di-O-(α-l-arabinofuranosyl)-β-d-galactopyranosyl-(1→6)-d-galactoses

  摘要：

  For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide alpha-L-Araf-(1 --> 2)-beta-D-Galp-(1 --> 6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl- (1 --> 6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, alpha-L-Araf-(1 --> 6)-beta-D-Galp-(1 --> 6)-D-Gal and (alpha-L-Araf)(2)-(1 --> 2,6)-beta-D-Galp-(1 --> 6)-D-Gal were also synthesized and characterised. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00094-4
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide 、 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 氰化汞 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以24.7%的产率得到2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1-> 2)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1-> 6)]-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2′-O-, 6′-O- and 2′,6′-di-O-(α-l-arabinofuranosyl)-β-d-galactopyranosyl-(1→6)-d-galactoses

  摘要：

  For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide alpha-L-Araf-(1 --> 2)-beta-D-Galp-(1 --> 6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl- (1 --> 6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, alpha-L-Araf-(1 --> 6)-beta-D-Galp-(1 --> 6)-D-Gal and (alpha-L-Araf)(2)-(1 --> 2,6)-beta-D-Galp-(1 --> 6)-D-Gal were also synthesized and characterised. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00094-4