2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl isonitrile | 62131-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl isonitrile
• 英文别名: (2R,3R,4S,5R,6R)-2-isocyano-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 62131-31-1
• 化学式: C₃₅H₃₅NO₅
• 分子量: 549.667
• InChiKey: JGNABDHPVLQKFE-CKQPALCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-2-氨基乙醛 、 溶剂黄146 、 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl isonitrile 反应 144.0h， 以31%的产率得到N-(2-acetoxy-3-t-butoxycarbobylamido-propionyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl amine
  参考文献：
  名称：

  Passerini and Ugi reactions of anomeric glucosyl isonitriles

  摘要：

  Acetyl and benzyl protected beta-D-glucopyranosyl isonitriles were treated with various aldehydes and acetic acid to give the corresponding Passerini reaction products and with i-butanal, carboxylic acids and amines to give the corresponding Ugi reaction products, respectively. No significant diastereoselectivity was observed for both reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01216-7
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl amine 、 甲乙酐 在 三乙胺 、 氯甲酸三氯甲酯 作用下， 以 乙酸乙酯 、 二氯甲烷 为溶剂， 反应 18.0h， 以83%的产率得到2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl isonitrile
  参考文献：
  名称：

  Passerini and Ugi reactions of benzyl and acetyl protected isocyanoglucoses

  摘要：

  Acetyl and benzyl protected anomeric beta-D-glucopyranosyl isonitriles and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-isocyano-beta-D-glucopyranose were treated with various carbonyl compounds and carboxylic acids to give the corresponding Passerini reaction products and with i-butanal, carboxylic acids and amines or aminoacids to give the corresponding Ugi reaction products, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00461-5