methyl 3-O-benzyl-6-(3-O-benzyl-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside | 153596-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-6-(3-O-benzyl-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: methyl 4-O-(4-O-benzoyl-3-O-benzyl-6-deoxy-β-D-arabino-hexopyranosyl)-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside
• CAS: 153596-69-1
• 化学式: C₃₄H₄₀O₈
• 分子量: 576.687
• InChiKey: KOQKKKURGZCCPX-PZJXYSNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-6-(3-O-benzyl-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside 在 sodium 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以77%的产率得到methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of a terminal A-B-C disaccharide fragment of flambamycin, curamycin, and avilamycin

  摘要：

  Methyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-beta-D-arabino-hexopyranosyl]-alpha-D-arabino-hexopyranoside (25) corresponds to an A-B-C disaccharide subunit of the title antibiotics. It was synthesized from suitably protected monosaccharide and aromatic precursors. The readily available 4,6-O-benzylidene-1,2-O-(R)-propylidene-alpha-D-glucopyranose was converted in six steps into 2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-alpha-D-glucopyranosyl bromide, which was condensed with methyl 3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside in the presence of mercury(II) cyanide. Methyl 4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-beta-D-glucopyranosyl)-3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside was converted either into methyl 2,6-dideoxy-4-O-(6-deoxy-beta-D-glucopyranosyl)-alpha-D-arabino-hexopyranoside by removal of the protective groups or into methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-beta-D-arabino-hexopyranosyl)-2,6-dideoxy-alpha-D-arabino-hexopyranoside (22) by selective deacetylation, Barton deoxygenation, and Zemplen debenzoylation. Disaccharide 22 was deprotonated with butyllithium and treated with 4-benzyloxy-3,5-dichloro-2-methoxy-6-methylbenzoyl chloride to give the title compound 25 after hydrogenolysis.

  DOI：

  10.1016/0008-6215(93)84119-q
• 作为产物：
  描述：

  Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 70.5h， 生成 methyl 3-O-benzyl-6-(3-O-benzyl-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of a terminal A-B-C disaccharide fragment of flambamycin, curamycin, and avilamycin

  摘要：

  Methyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-beta-D-arabino-hexopyranosyl]-alpha-D-arabino-hexopyranoside (25) corresponds to an A-B-C disaccharide subunit of the title antibiotics. It was synthesized from suitably protected monosaccharide and aromatic precursors. The readily available 4,6-O-benzylidene-1,2-O-(R)-propylidene-alpha-D-glucopyranose was converted in six steps into 2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-alpha-D-glucopyranosyl bromide, which was condensed with methyl 3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside in the presence of mercury(II) cyanide. Methyl 4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-beta-D-glucopyranosyl)-3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside was converted either into methyl 2,6-dideoxy-4-O-(6-deoxy-beta-D-glucopyranosyl)-alpha-D-arabino-hexopyranoside by removal of the protective groups or into methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-beta-D-arabino-hexopyranosyl)-2,6-dideoxy-alpha-D-arabino-hexopyranoside (22) by selective deacetylation, Barton deoxygenation, and Zemplen debenzoylation. Disaccharide 22 was deprotonated with butyllithium and treated with 4-benzyloxy-3,5-dichloro-2-methoxy-6-methylbenzoyl chloride to give the title compound 25 after hydrogenolysis.

  DOI：

  10.1016/0008-6215(93)84119-q

文献信息

• Environmentally benign β-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10
  作者：Hideyuki Nagai、Kaname Sasaki、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.carres.2004.11.025

  日期：2005.2

  Environmentally benign and stereoselective beta-glycosidations of glycopyranosyl phosphites and alcohols using a reusable heterogeneous solid acid, montmorillonite K-10, as an activator have been developed. By these glycosidations, beta-gluco-, 2-deoxy-betagluco-, and beta-mannopyrano sides were selectively produced in good to high yields. (C) 2004 Elsevier Ltd. All rights reserved.