1,5-anhydro-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine | 610314-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine
• 英文别名: diethyl 2-[[(1R,2R,6R,7R)-4,4-dimethyl-3,5,10-trioxa-8-azatricyclo[5.2.1.02,6]decan-8-yl]methylidene]propanedioate
• CAS: 610314-61-9
• 化学式: C₁₆H₂₃NO₇
• 分子量: 341.361
• InChiKey: XJCQFGAWEAUITB-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  丁硫醇 、 1,5-anhydro-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以84%的产率得到(2S,3R,4R,5R)-2-butylthio-N-(2,2-diethoxycarbonylvinyl)-5-hydroxy-3,4-(isopropylidenedioxy)piperidine
  参考文献：
  名称：

  d-Ribofuranosylenamine: a versatile starting material for preparing azasugar thioglycosides and building blocks for thioureylene-di-nucleosides

  摘要：

  Six-membered azasugar thioglycosides (piperidines) are prepared from a beta-D-ribofuranosylenamine, with a 1,5-anhydro derivative being the key intermediate. The alpha-anomer of the same D-ribofuranosylenamine is transformed into a 5-deoxy-5-isothiocyanato derivative, useful for preparing D-ribosylamino derivatives with a non-ionic thiourea bridge, isosteric of the phosphate bridge. The prepared thioureas are potential building blocks for the synthesis of thioureylene-di-nucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.012
• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-D-ribofuranosylamine 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、2.67 kPa 条件下， 反应 0.25h， 以91%的产率得到1,5-anhydro-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine
  参考文献：
  名称：

  d-Ribofuranosylenamine: a versatile starting material for preparing azasugar thioglycosides and building blocks for thioureylene-di-nucleosides

  摘要：

  Six-membered azasugar thioglycosides (piperidines) are prepared from a beta-D-ribofuranosylenamine, with a 1,5-anhydro derivative being the key intermediate. The alpha-anomer of the same D-ribofuranosylenamine is transformed into a 5-deoxy-5-isothiocyanato derivative, useful for preparing D-ribosylamino derivatives with a non-ionic thiourea bridge, isosteric of the phosphate bridge. The prepared thioureas are potential building blocks for the synthesis of thioureylene-di-nucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.012

文献信息

• The use of anhydroiminocyclitols as glycosyl donors in glycosidation reactions
  作者：José Fuentes、Nader R. Al Bujuq、Manuel Angulo、Consolación Gasch

  DOI：10.1016/j.tet.2010.09.065

  日期：2010.11

  iminosugar thioglycosides by nucleophilic opening of both new and previously described N-diethoxycarbonylvinyl anhydroiminosugar derivatives (glycosyl donors) with primary alcohols, primary thiols, and thiophenol (glycosyl acceptors) is reported. The reactions are highly stereoselective, with anomeric ratios better than 4:1.

  通过新的和先前描述的N-二乙氧基羰基乙烯基脱水亚氨基糖衍生物（糖基供体）与伯醇，伯硫醇和硫酚（亲核打开）的高产合成六元和五元N-取代的亚氨基糖苷和五元亚氨基糖硫糖苷糖基受体）的报道。该反应是高度立体选择性的，端基异构体比率优于4：1。
• Stereoselective synthesis of azasugar thioglycosides
  作者：M.Angeles Pradera、Francisco J. Sayago、José M. Illangua、Consolación Gasch、José Fuentes

  DOI：10.1016/s0040-4039(03)01685-x

  日期：2003.8

  Bicyclic (2-oxapyrrolizidines) and monocyclic (piperidine) azasugar ethyl thioglycosides, a new type of azasugar derivative, are stereoselectively prepared from suitable glycosylenamines, through anhydroazasugar derivatives. (C) 2003 Elsevier Ltd. All rights reserved.
• Iminosugar thioglycosides as glycosyl donors: a route to disaccharides with an iminosugar moiety
  作者：José Fuentes、Nader R. Al Bujuq、Manuel Angulo、Consolación Gasch

  DOI：10.1016/j.tetlet.2007.11.160

  日期：2008.1

  The immosugar thioglycosides are used as glycosyl donors in glycosidation reactions. Thereby, iminosugar glycosides and disaccharide analogues with an iminosugar moiety are prepared. The yields are high and the method is stereoselective. (C) 2007 Elsevier Ltd. All rights reserved.
• d-Ribofuranosylenamine: a versatile starting material for preparing azasugar thioglycosides and building blocks for thioureylene-di-nucleosides
  作者：José Fuentes、José M. Illangua、Francisco J. Sayago、Manuel Angulo、Consolación Gasch、M. Ángeles Pradera

  DOI：10.1016/j.tetasy.2004.10.012

  日期：2004.11

  Six-membered azasugar thioglycosides (piperidines) are prepared from a beta-D-ribofuranosylenamine, with a 1,5-anhydro derivative being the key intermediate. The alpha-anomer of the same D-ribofuranosylenamine is transformed into a 5-deoxy-5-isothiocyanato derivative, useful for preparing D-ribosylamino derivatives with a non-ionic thiourea bridge, isosteric of the phosphate bridge. The prepared thioureas are potential building blocks for the synthesis of thioureylene-di-nucleosides. (C) 2004 Elsevier Ltd. All rights reserved.