benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 868161-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,4aR,6R,7R,8R,8aS)-2-phenyl-6,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 868161-61-9
• 化学式: C₂₉H₃₁NO₆
• 分子量: 489.568
• InChiKey: LMMOQGCMJGSYAM-PADYGVHUSA-N

物化性质

• 沸点：
  678.0±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 吡啶 、 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 copper(l) iodide 、 叠氮基三甲基硅烷 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 四氯化锡 、 N,N-二异丙基乙胺 、 barium(II) hydroxide 、 barium(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.0h， 生成 methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-azidooxan-3-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 sodium methylate 、 对甲苯磺酸 、 barium(II) hydroxide 、 barium(II) oxide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z

文献信息

• New deprotection method of the 2,2,2-trichloroethoxycarbonyl (Troc) group with (Bu3Sn)2
  作者：Hiroomi Tokimoto、Koichi Fukase

  DOI：10.1016/j.tetlet.2005.08.026

  日期：2005.10

  The 2.2,2-trichloroethoxycarbonyl (Troc) group was efficiently removed in high yields with (BU3Sn)(2) in DMF under microwave heating. The present method was applied to deprotection of the Troc group on solid support. (c) 2005 Elsevier Ltd. All rights reserved.
• Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks
  作者：Smritilekha Bera、Robert J. Linhardt

  DOI：10.1021/jo200076z

  日期：2011.5.6

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.