N-((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-acetamide | 113084-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-acetamide
• CAS: 113084-98-3
• 化学式: C₃₇H₄₁NO₆
• 分子量: 595.736
• InChiKey: FWZUEVHMEGJWAR-KHKVHWIZSA-N

物化性质

• 沸点：
  745.1±60.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-acetamide 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以98.9%的产率得到1-acetamide-2,6-anhydro-D-glycero-D-ido-heptitol
  参考文献：
  名称：

  Recognition Properties of Processing α‐Glucosidase I and α‐Glucosidase II

  摘要：

  All four possible monodeoxy derivatives of p-nitrophenyl alpha-D-glucopyranoside (PNP Glc) and 1-amino-2,6-anhydro-1-deOXY-D-glycero-D-ido-heptitol derivatives were prepared and used as substrates and inhibitors of rat liver processing alpha-glucosidases. alpha-Glucosidase II hydrolyzed the 2-deoxy derivative of PNP Glc (1); the hydrolysis of 1 was more rapid than that of PNP Glc. These results indicate that the presence of a C-2 hydroxyl group is not essential for the action of alpha-glucosidase II. In contrast, PNP Glc and all of the deoxy derivatives of PNP Glc 1-4 inhibited alpha-glucosidase I. These results indicate that alpha-glucosidase I does not necessarily need all of the hydroxyl groups of the glycon moiety for binding to the enzyme. 2,6-Anhydro-1-benzamide-D-glycero-D-ido-heptitol (11), with a terminal phenyl group, inhibited a-glucosidase I and a-glucosidase II. Both alpha-glucosidase I and II showed the same aglycon specificities. When probes 5-12 were assayed for their ability to inhibit processing by a-glucosidases at the cellular level, no effects on glycoprotein processing were observed.

  DOI：

  10.1081/car-120030022
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl cyanide 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-((2R,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-acetamide
  参考文献：
  名称：

  Recognition Properties of Processing α‐Glucosidase I and α‐Glucosidase II

  摘要：

  All four possible monodeoxy derivatives of p-nitrophenyl alpha-D-glucopyranoside (PNP Glc) and 1-amino-2,6-anhydro-1-deOXY-D-glycero-D-ido-heptitol derivatives were prepared and used as substrates and inhibitors of rat liver processing alpha-glucosidases. alpha-Glucosidase II hydrolyzed the 2-deoxy derivative of PNP Glc (1); the hydrolysis of 1 was more rapid than that of PNP Glc. These results indicate that the presence of a C-2 hydroxyl group is not essential for the action of alpha-glucosidase II. In contrast, PNP Glc and all of the deoxy derivatives of PNP Glc 1-4 inhibited alpha-glucosidase I. These results indicate that alpha-glucosidase I does not necessarily need all of the hydroxyl groups of the glycon moiety for binding to the enzyme. 2,6-Anhydro-1-benzamide-D-glycero-D-ido-heptitol (11), with a terminal phenyl group, inhibited a-glucosidase I and a-glucosidase II. Both alpha-glucosidase I and II showed the same aglycon specificities. When probes 5-12 were assayed for their ability to inhibit processing by a-glucosidases at the cellular level, no effects on glycoprotein processing were observed.

  DOI：

  10.1081/car-120030022