2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyl azide | 288844-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyl azide
• 英文别名: [(2R,3R,4S,5R,6R)-6-azido-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 288844-57-5
• 化学式: C₂₈H₃₁N₃O₆
• 分子量: 505.571
• InChiKey: JBCQILBZUBDBNF-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(p-nitrophenylcarbamate)-ethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 、 2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyl azide 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以94%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[[[(2R,3R,4S,5R,6R)-6-azido-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)oxan-2-yl]methoxycarbonyl-[2-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyethyl]carbamoyl]amino]ethoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of Allophanate-Derived Branched Glycoforms from Alcohols and p-Nitrophenyl Carbamates

  摘要：

  [GRAPHICS]The formation of saccharide derived carbamates and alkyl 2,4-dialkylallophanates from alcohols and p-nitrophenyl carbamates is described. Optimization of allophanate formation has led to the synthesis of branched glycoforms with inter saccharide allophanate linkages that are rigidified by intramolecular hydrogen bonds.

  DOI：

  10.1021/ol0060127
• 作为产物：
  描述：

  2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-glucopyranosyl azide 在 三甲基氯硅烷 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以93%的产率得到2,3-di-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of Allophanate-Derived Branched Glycoforms from Alcohols and p-Nitrophenyl Carbamates

  摘要：

  [GRAPHICS]The formation of saccharide derived carbamates and alkyl 2,4-dialkylallophanates from alcohols and p-nitrophenyl carbamates is described. Optimization of allophanate formation has led to the synthesis of branched glycoforms with inter saccharide allophanate linkages that are rigidified by intramolecular hydrogen bonds.

  DOI：

  10.1021/ol0060127

文献信息

• Synthesis of Allophanate-Derived Branched Glycoforms from Alcohols and<i> p</i>-Nitrophenyl Carbamates
  作者：Pek Y. Chong、Peter A. Petillo

  DOI：10.1021/ol0060127

  日期：2000.7.1

  [GRAPHICS]The formation of saccharide derived carbamates and alkyl 2,4-dialkylallophanates from alcohols and p-nitrophenyl carbamates is described. Optimization of allophanate formation has led to the synthesis of branched glycoforms with inter saccharide allophanate linkages that are rigidified by intramolecular hydrogen bonds.