(R)-2-((S)-1-phenylethylamino)-2-C-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)acetonitrile | 1352561-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-((S)-1-phenylethylamino)-2-C-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)acetonitrile
• CAS: 1352561-40-0
• 化学式: C₄₄H₄₆N₂O₅
• 分子量: 682.86
• InChiKey: ONAURRWPSCEFHT-WZEOZZSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.97
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 2,6-Anhydro-3,4,5,7-tetra-O-benzyl-aldehydo-D-glycero-D-ido-heptopyranose 、 丙酮氰醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 (S)-2-((S)-1-phenylethylamino)-2-C-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)acetonitrile 、 (R)-2-((S)-1-phenylethylamino)-2-C-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)acetonitrile
  参考文献：
  名称：

  Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction

  摘要：

  Synthesis of new 2-amino-2-C-D-glycosyl-acetonitriles in a Strecker reaction from various C-glycosyl aldehydes, chiral amines, and HCN was carried out. While aminonitriles from glycal and 2-deoxy-beta-D-glycosyl aldehydes were prepared in satisfactory yields, lower yields were obtained with C-glycosyl aldehydes. Strecker reaction with the benzyl-protected 1-C-formyl-D-galactal and S- or R-1-phenylethylamine (S-PEA or R-PEA) yielded predominantly the R-configured C-glycosyl aminoacetonitrile. The direction of the nucleophilic addition appears to be governed by the configuration of the anomeric carbon with beta-linked sugars. Since the stereochemistry of the transition state is unknown according to the configuration of the major product a Felkin-Ahn selectivity can be mainly presumed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.023