2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-mesyl-β-D-mannopyranosylamine | 488827-80-1

• 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)-6-O-mesyl-β-D-mannopyranosylamine
• 英文别名: diethyl 2-[[[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(methylsulfonyloxymethyl)oxan-2-yl]amino]methylidene]propanedioate
• CAS: 488827-80-1
• 化学式: C₃₆H₃₇NO₁₄S
• 分子量: 739.754
• InChiKey: PMBUOEVDNSOFSD-ZOROSQJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  205
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-mesyl-β-D-mannopyranosylamine 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、2.67 kPa 条件下， 反应 4.25h， 生成 1,6-anhydro-N-(2,2-diethoxycarbonylvinyl)-β-D-mannopyranosylamine
  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：

  2-[((2R,3S,4S,5S,6R)-3,4,5-Trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-ylamino)-methylene]-malonic acid diethyl ester 在 吡啶 、 三氟乙酸 作用下， 反应 48.08h， 生成 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-mesyl-β-D-mannopyranosylamine
  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

文献信息

• Efficient synthesis of seven-membered iminocyclitols from glycosylenamines
  作者：José Fuentes、David Olano、M.Angeles Pradera

  DOI：10.1016/s0040-4039(99)00649-8

  日期：1999.5

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.