(2R,3R,4R,5R)-5-((R)-1-azido-2-(benzyloxy)ethyl)-4-(benzyloxy)tetrahydrofuran-2,3-diol | 115351-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-5-((R)-1-azido-2-(benzyloxy)ethyl)-4-(benzyloxy)tetrahydrofuran-2,3-diol
• CAS: 115351-20-7
• 化学式: C₂₀H₂₃N₃O₅
• 分子量: 385.42
• InChiKey: CSJWWRPDIAJYEY-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116.91
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,2-O-isopropylidene-3,6-di-O-benzyl-5-azido-5-deoxy-α-D-glucofuranose 在 水 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 (2S,3R,4R,5R)-5-[(1R)-1-azido-2-phenylmethoxyethyl]-4-phenylmethoxyoxolane-2,3-diol 、 (2R,3R,4R,5R)-5-((R)-1-azido-2-(benzyloxy)ethyl)-4-(benzyloxy)tetrahydrofuran-2,3-diol
  参考文献：
  名称：

  Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-l-bulgecinine from d-glucuronolactone and of l-DNJ, l-DMDP, and (3S)-3-hydroxy-d-bulgecinine from l-glucuronolactone. DMDP inhibits β-glucosidases and β-galactosidases whereas l-DMDP is a potent and specific inhibitor of α-glucosidases

  摘要：

  A convenient large-scale synthesis of 1-deoxynojirimyin (DNJ) from D-glucuronolactone involves introduction of azide at C-5 with retention of configuration to give 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose as a key intermediate in an overall yield of up to 72%; the same intermediate can be transformed into DMDP (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol] and (3R)-3-hydroxy-L-bulgecinine [(2S,3R,4R,5R)-3,4-dihydroxy-5-hydroxymethyl-L-proline]. L-Glucuronolactone, a readily available L-sugar chiron, may similarly be used to access the enantiomers L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine. A comparison of glycosidase inhibition by DMDP (an inhibitor of beta-glucosidases and beta-galactosidases) and L-DMDP (a potent and specific alpha-glucosidase inhibitor) with the corresponding enantiomeric hydroxybulgecinines is reported; DMDP and (3R)-3-hydroxy-L-bulgecinine show weak inhibition of glycogen phosphorylase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.017