7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol | 155101-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol
• CAS: 155101-40-9
• 化学式: C₄₁H₄₃NO₅
• 分子量: 629.796
• InChiKey: WQBSQISTAIQYOD-NBUXTFBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙酸乙酯 为溶剂， 反应 22.0h， 生成 1,3,4,5-tetra-O-acetyl-2,6-anhydro-7-tert-butoxycarbonylamino-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol
  参考文献：
  名称：

  Aminosubstituted α-d-glucosylmethylbenzenes (benzyl α-C-glucosides) and an N-(C-α-d-glucosylmethyl)aniline (anilinomethyl α-C-glucoside); novel α-d-glucosidase inhibitors

  摘要：

  D-Glucose was transformed via 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-gluco-hept-1-enitol (5) into 2,6-anhydro-3-4-5,7,tetra-O-benzyl-1-C-phenyl-D-erythro-L-ido-heptitol (9) the structure of which was determined by X-ray analysis of the per-O-acetylated derivative 12. 1-O-Mesylation of 9 and azide displacement gave only low yields of 2,6-anhydro-7-azido-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol (16). Therefore, 9 was oxidized to 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-phenyl-D-glycero-D-ido-heptose (15) and thence transformed into the (E/Z)-oximes 17h,l which, with LiAlH4 as reducing agent, gave 7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol (19), 7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-L-threo-L-gulo-heptitol (23), and 2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-phenylamino-D-glycero-L-gulo-heptitol (27) in 1:1:1 ratios. Their N-protection, hydrogenolytic O-debenzylation, and N-deprotection afforded the desired target molecules 7-amino-2,6-anhydro-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol (1a), 7-amino-2,6-anhydro-7-deoxy-7-C-phenyl-L-threo-L-gulo-heptitol (2a), and 2,6-anhydro-7-deoxy-7-phenyl-amino-D-glycero-L-gulo-heptitol (4a). Hydrogenolysis of 15 furnished directly 2,6-anhydro-7-deoxy-7-C-phenyl-D-glycero-L-gulo-heptitol (3a). Inhibition studies with alpha-D-glucosidase from yeast with p-nitrophenyl alpha-D-glucopyranoside as substrate exhibited, for 1a and 4a, K-i values of the same order as found for 1-deoxynojirimycin.

  DOI：

  10.1016/0008-6215(93)84163-z
• 作为产物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-methanesulfonyl-1-C-phenyl-D-erythro-L-ido-heptitol 在 lithium aluminium tetrahydride 、 tetramethylguanidinum azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 169.5h， 生成 7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol
  参考文献：
  名称：

  Aminosubstituted α-d-glucosylmethylbenzenes (benzyl α-C-glucosides) and an N-(C-α-d-glucosylmethyl)aniline (anilinomethyl α-C-glucoside); novel α-d-glucosidase inhibitors

  摘要：

  D-Glucose was transformed via 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-D-gluco-hept-1-enitol (5) into 2,6-anhydro-3-4-5,7,tetra-O-benzyl-1-C-phenyl-D-erythro-L-ido-heptitol (9) the structure of which was determined by X-ray analysis of the per-O-acetylated derivative 12. 1-O-Mesylation of 9 and azide displacement gave only low yields of 2,6-anhydro-7-azido-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol (16). Therefore, 9 was oxidized to 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-C-phenyl-D-glycero-D-ido-heptose (15) and thence transformed into the (E/Z)-oximes 17h,l which, with LiAlH4 as reducing agent, gave 7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol (19), 7-amino-2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-C-phenyl-L-threo-L-gulo-heptitol (23), and 2,6-anhydro-1,3,4,5-tetra-O-benzyl-7-deoxy-7-phenylamino-D-glycero-L-gulo-heptitol (27) in 1:1:1 ratios. Their N-protection, hydrogenolytic O-debenzylation, and N-deprotection afforded the desired target molecules 7-amino-2,6-anhydro-7-deoxy-7-C-phenyl-D-erythro-L-gulo-heptitol (1a), 7-amino-2,6-anhydro-7-deoxy-7-C-phenyl-L-threo-L-gulo-heptitol (2a), and 2,6-anhydro-7-deoxy-7-phenyl-amino-D-glycero-L-gulo-heptitol (4a). Hydrogenolysis of 15 furnished directly 2,6-anhydro-7-deoxy-7-C-phenyl-D-glycero-L-gulo-heptitol (3a). Inhibition studies with alpha-D-glucosidase from yeast with p-nitrophenyl alpha-D-glucopyranoside as substrate exhibited, for 1a and 4a, K-i values of the same order as found for 1-deoxynojirimycin.

  DOI：

  10.1016/0008-6215(93)84163-z