N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine | 157306-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine
• 英文别名: N-2,2-diethoxycarbonylvinyl-2,3-O-isopropylidene-β-D-ribofuranosylamine；2,3-O-isopropylidene-N-(2,2-diethoxycarbonylvinyl)-β-D-ribofuranosylamine；diethyl 2-[[[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]amino]methylidene]propanedioate
• CAS: 157306-01-9
• 化学式: C₁₆H₂₅NO₈
• 分子量: 359.376
• InChiKey: RTBHFFLEWRTMNG-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 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 15.25h， 生成 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
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-ribofuranosylamine toluene-p-sulphonate 、 乙氧基甲叉丙二酸二乙酯 在 sodium methylate 作用下， 生成 N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 、 N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-α-D-ribofuranosylamine
  参考文献：
  名称：

  D-呋喃呋喃糖基胺作为糖基受体。

  摘要：

  DOI：

  10.1016/0008-6215(94)80044-8

文献信息

• 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.
• A d-ribofuranosylenamine as glycosyl acceptor
  作者：Jose Fuentes Mota、Danuta Mostowicz、Carmen Ortiz、M. Angeles Pradera、Inmaculada Robina

  DOI：10.1016/0008-6215(94)80044-8

  日期：1994.5