O-(2,3,4-Tri-O-acetyl-6-deoxy-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose | 29487-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-Tri-O-acetyl-6-deoxy-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose
• 英文别名: 6'-Deoxy-hepta-O-acetylmaltose；Hepta-O-acetyl-6'-desoxy-β-maltose
• CAS: 29487-68-1
• 化学式: C₂₆H₃₆O₁₇
• 分子量: 620.562
• InChiKey: IOMNMBCINQNMCJ-FNBSJMBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-Tri-O-acetyl-6-deoxy-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以66%的产率得到Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes

  摘要：

  The four derivatives of beta-maltosyl-(1 --> 4)-trehalose have been synthesized, which are monodeoxygenated at the site of one of the primary hydroxyl groups. The tetrasaccharides were constructed in [2+2] block syntheses. Thus, 6'''-deoxy-beta-maltosyl-(1 --> 4)-trehalose was prepared by selective iodination of allyl 2,3,6,2',3'-penta-O-acetyl-beta-maltoside (3) followed by catalytic hydrogenolysis and coupling with 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-benzyl-alpha-D-glucopyranoside (9), and 6 ''-deoxy-beta-maltosyl-(1 --> 4)-trehalose by selective iodination of allyl 4',6'-O-isopropylidene-beta-maltoside (14), coupling with 9, and one-step hydrogenolysis at the tetrasaccharide level. For the synthesis of 6'-deoxy-beta-maltosyl-(1 --> 4)-trehalose, the diol 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3'-di-O-benzyl-alpha-D-glucopyranoside (22) was selectively iodinated and glycosylated with acetobromomaltose followed by catalytic hydrogenolysis. The 6-deoxy-beta-maltosyl-(1 --> 4)-trehalose was obtained upon selective iodination of a tetrasaccharide diol.

  DOI：

  10.1080/07328309608005672
• 作为产物：
  描述：

  O-(2,3,4-Tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以90%的产率得到O-(2,3,4-Tri-O-acetyl-6-deoxy-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  Selectively Deoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose as Biological Probes

  摘要：

  The four derivatives of beta-maltosyl-(1 --> 4)-trehalose have been synthesized, which are monodeoxygenated at the site of one of the primary hydroxyl groups. The tetrasaccharides were constructed in [2+2] block syntheses. Thus, 6'''-deoxy-beta-maltosyl-(1 --> 4)-trehalose was prepared by selective iodination of allyl 2,3,6,2',3'-penta-O-acetyl-beta-maltoside (3) followed by catalytic hydrogenolysis and coupling with 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-benzyl-alpha-D-glucopyranoside (9), and 6 ''-deoxy-beta-maltosyl-(1 --> 4)-trehalose by selective iodination of allyl 4',6'-O-isopropylidene-beta-maltoside (14), coupling with 9, and one-step hydrogenolysis at the tetrasaccharide level. For the synthesis of 6'-deoxy-beta-maltosyl-(1 --> 4)-trehalose, the diol 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3'-di-O-benzyl-alpha-D-glucopyranoside (22) was selectively iodinated and glycosylated with acetobromomaltose followed by catalytic hydrogenolysis. The 6-deoxy-beta-maltosyl-(1 --> 4)-trehalose was obtained upon selective iodination of a tetrasaccharide diol.

  DOI：

  10.1080/07328309608005672