(R)-2-(benzyloxy)-1-penylethyl 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-L-arabino-hexopyranoside | 1314380-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-(benzyloxy)-1-penylethyl 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-L-arabino-hexopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[[(2S,3R,4S,6S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(1R)-1-phenyl-2-phenylmethoxyethoxy]oxan-4-yl]methyl]oxane
• CAS: 1314380-17-0
• 化学式: C₇₀H₇₄O₁₀
• 分子量: 1075.35
• InChiKey: QJOHGUXOSQAWKH-LVDGWAHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  80
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R)-2-(benzyloxy)-1-penylethyl 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-L-arabino-hexopyranoside 、 苯硫酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-L-arabino-hexopyranoside 、 phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-L-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：

  2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)ethyl aldehyde 在 lithium aluminium tetrahydride 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 sodium hydride 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 、 mineral oil 为溶剂， 反应 152.33h， 生成 (R)-2-(benzyloxy)-1-penylethyl 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-L-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