2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 249511-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: [(3aS,4R,6R,7R,7aS)-2,2-dimethyl-7-phenylmethoxy-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]methanol
• CAS: 249511-82-8
• 化学式: C₂₈H₄₀O₁₁
• 分子量: 552.619
• InChiKey: MIOXHFPOQKTMKE-NZVDZQMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium methylate 、 氰化汞 、 对甲苯磺酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 [(3aS,4R,6R,7R,7aS)-6-[[(3aS,4R,6R,7R,7aS)-2,2-dimethyl-7-phenylmethoxy-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]-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
  参考文献：
  名称：

  Synthesis of an arabinogalactan-type octa- and two isomeric nonasaccharides. Suitable tuning of protecting groups

  摘要：

  An arabinogalactan-type double-branched octa- and two isomeric nonasaccharides were synthesized using the (2-naphthyl)methyl (NAP) and the acid sensitive but base stable (methoxydimethyl)methyl (MIP) protecting groups. The beta-(1-->6)-linked hexagalactan skeleton was synthesized having a benzyl and a (2-naphthyl)methyl (NAP) group at positions 2 of the second and the penultimate galactopyranosyl units, and this made possible sequential introduction Of U-L-arabinofuranosyl or alpha-L-arabinofuranosyl-(1-->5)-alpha-L-arabinofuranosyl side chains. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02723-5
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 2-O-benzyl-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