(E)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one | 1314380-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one
• 英文别名: (E)-1-(1,3-thiazol-2-yl)-4-[(2S,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]but-2-en-1-one
• CAS: 1314380-02-3
• 化学式: C₄₁H₄₁NO₆S
• 分子量: 675.846
• InChiKey: XBCCHPJIHGJNIL-QPZQNTTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one 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 、 乙腈 、 mineral oil 为溶剂， 反应 44.83h， 生成 (2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-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
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-D-mannopyranosyl)-ethanal 、 1-(thiazol-2-yl)-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 以 氯仿 为溶剂， 反应 30.0h， 以3.8 g的产率得到(E)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one
  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

文献信息

• Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound
  作者：Zuzana Lövyova、Kamil Parkan、Ladislav Kniežo

  DOI：10.1016/j.tet.2011.04.044

  日期：2011.7

  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.