5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-isothiocyanato-α-D-ribofuranosylamine | 828249-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-isothiocyanato-α-D-ribofuranosylamine
• 英文别名: diethyl 2-[[[(3aR,4S,6R,6aR)-6-(isothiocyanatomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]amino]methylidene]propanedioate
• CAS: 828249-11-2
• 化学式: C₁₇H₂₄N₂O₇S
• 分子量: 400.453
• InChiKey: CXZMYJSKHPEPMS-SYQHCUMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S)-4'-acetyl-4-amino-5'-methyl-2,3,4,5-tetrahydro-[2,2']bifuranyl-3-yl ester 、 5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-isothiocyanato-α-D-ribofuranosylamine 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以94%的产率得到N-[2-O-acetyl-1,3-dideoxy-1-(3''-acetyl-2''-methylfur-5''-yl)-α-L-threofuranos-3-yl],N'-[1-(2,2-diethoxycarbonylvinylamino)-2,3-O-isopropylidene-1-deoxy-α-D-ribofuranos-5-yl] thiourea
  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-α-D-ribofuranosylamine 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 甲基磺酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-isothiocyanato-α-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

• 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.