orthoester of maltose | 41355-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: orthoester of maltose
• 英文别名: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose；[(3aR,5R,6R,7S,7aR)-7-acetyloxy-2-methoxy-2-methyl-6-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• CAS: 41355-74-2
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: ZCYIOMNMBFPZBH-FRGIIGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  orthoester of maltose 在 sodium methylate 作用下， 以 甲醇 、 氯苯 为溶剂， 反应 14.0h， 生成 2-<4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyloxy>-3-hydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Autocatalytic condensation of 1,2-orthoesters of sugars with 2,3-dihydroxy-1,4-naphthoquinone (isonaphthazarin)

  摘要：

  DOI：

  10.1007/bf00597646
• 作为产物：
  描述：

  甲醇 、 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 在 4-二甲氨基吡啶 、 四丁基溴化铵 作用下， 反应 22.0h， 以64%的产率得到orthoester of maltose
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113

文献信息

• Synthesis of acetylated glycosides of 2,3-dihydroxy-1,4-naphthoquinone
  作者：S. G. Golonik、A. M. Tolkach、N. I. Uvarova

  DOI：10.1007/bf00574825

  日期：——
• POLONIK, S. G.;TOLKACH, A. M.;UVAROVA, N. I., XIMIYA PRIROD. SOED.,(1989) N, S. 477-482
  作者：POLONIK, S. G.、TOLKACH, A. M.、UVAROVA, N. I.

  DOI：——

  日期：——