2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine | 144310-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine
• 英文别名: diethyl 2-[[[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(hydroxymethyl)oxan-2-yl]amino]methylidene]propanedioate
• CAS: 144310-56-5
• 化学式: C₃₅H₃₅NO₁₂
• 分子量: 661.662
• InChiKey: ODWQHSZPDLZNNK-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 吡啶 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、2.67 kPa 条件下， 反应 24.25h， 生成 1,6-anhydro-2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines

  摘要：

  A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazelpines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropyranose derivatives. O- and N-Deprotection of the latter, followed by reduction with sodium cyanoborohydride, gives the target chiral iminocyclitols. The method is based on the capacity of the dialkoxycarbonylvinyl group to stabilize an amide ion, and the only limitation is the necessity for the starting glycosylenamine to have beta-D-configuration. The inhibitory activity of several intermediate iminocyclitols and aldopyranosylenamines on different alpha- and beta-glycosidases is also reported. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00377-4
• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 吡啶 、 三氟乙酸 作用下， 反应 24.17h， 生成 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  葡萄糖基亚胺作为糖基受体：龙胆生物亚胺的合成

  摘要：

  2,3,4-三-O-苄基-（3），2,3,4-三-O-乙酰基-（4）和2,3,4-三-O-苯甲酰基-N-的制备描述了（2，2-二乙氧基羰基乙烯基）-6-O-三苯甲基-β-D-吡喃葡萄糖胺（5）。3-5与2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴化物的反应生成2,3,4-三-O-苄基-（9），2,3,4-三-O-乙酰基-（10）和2,3,4-三-O-苯甲酰基-N-（2,2-二乙氧基羰基乙烯基）-6-O-（2,3,4,6-tet ra-O -乙酰基-β-D-吡喃葡萄糖基）-β-D-吡喃葡糖基胺（11）。2,3,4-三-O-苄基-（6），2,3,4-三-O-乙酰基-（7）和2,3,4-三-O-苯甲酰基-N-（2，还描述了2-二乙氧基羰基乙烯基）-β-D-吡喃葡萄糖胺（8）。

  DOI：

  10.1016/s0008-6215(00)90993-5

文献信息

• Glucosylenamines as glycosyl acceptors: synthesis of gentiobiosylenamines
  作者：Jose Fuentes Mota、José Fernández-Bolaños Guzmán、José M. García Fernández、Wenceslao Moreda、Carmen Ortiz、M. Angeles Pradera、Inmaculada Robina、Colin Welsh

  DOI：10.1016/s0008-6215(00)90993-5

  日期：1992.7

  The preparation of 2,3,4-tri-O-benzyl- (3), 2,3,4-tri-O-acetyl- (4), and 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-trityl-beta- D-glucopyranosylamine (5) is described. The reaction of 3-5 with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide yields 2,3,4-tri-O-benzyl- (9), 2,3,4-tri-O-acetyl- (10), and 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-(2,3,4,6-tet ra-O- acetyl

  2,3,4-三-O-苄基-（3），2,3,4-三-O-乙酰基-（4）和2,3,4-三-O-苯甲酰基-N-的制备描述了（2，2-二乙氧基羰基乙烯基）-6-O-三苯甲基-β-D-吡喃葡萄糖胺（5）。3-5与2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴化物的反应生成2,3,4-三-O-苄基-（9），2,3,4-三-O-乙酰基-（10）和2,3,4-三-O-苯甲酰基-N-（2,2-二乙氧基羰基乙烯基）-6-O-（2,3,4,6-tet ra-O -乙酰基-β-D-吡喃葡萄糖基）-β-D-吡喃葡糖基胺（11）。2,3,4-三-O-苄基-（6），2,3,4-三-O-乙酰基-（7）和2,3,4-三-O-苯甲酰基-N-（2，还描述了2-二乙氧基羰基乙烯基）-β-D-吡喃葡萄糖胺（8）。
• An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines
  作者：José Fuentes、Consolación Gasch、David Olano、M.Ángeles Pradera、Guillermo Repetto、Francisco J. Sayago

  DOI：10.1016/s0957-4166(02)00377-4

  日期：2002.8

  A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazelpines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropyranose derivatives. O- and N-Deprotection of the latter, followed by reduction with sodium cyanoborohydride, gives the target chiral iminocyclitols. The method is based on the capacity of the dialkoxycarbonylvinyl group to stabilize an amide ion, and the only limitation is the necessity for the starting glycosylenamine to have beta-D-configuration. The inhibitory activity of several intermediate iminocyclitols and aldopyranosylenamines on different alpha- and beta-glycosidases is also reported. (C) 2002 Published by Elsevier Science Ltd.