(2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran | 1314380-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran
• CAS: 1314380-12-5
• 化学式: C₅₆H₅₈O₉
• 分子量: 875.071
• InChiKey: ULLYYSXVQQEYQV-OPKLAJECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.54
• 重原子数：
  65.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 35.5h， 生成 (S)-2-benzyloxy-1-phenylethyl 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

  摘要：

  The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -> 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.044
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 lithium aluminium tetrahydride 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 臭氧 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 、 mineral oil 为溶剂， 反应 232.16h， 生成 (2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

  摘要：

  The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -> 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.044