(2S,3R,4R,5R)-2-butylthio-N-(2,2-diethoxycarbonylvinyl)-5-hydroxy-3,4-(isopropylidenedioxy)piperidine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2-butylthio-N-(2,2-diethoxycarbonylvinyl)-5-hydroxy-3,4-(isopropylidenedioxy)piperidine
• 英文别名: diethyl 2-[[(3aR,4S,7R,7aR)-4-butylsulfanyl-7-hydroxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridin-5-yl]methylidene]propanedioate
• 化学式: C₂₀H₃₃NO₇S
• 分子量: 431.551
• InChiKey: PWFUPTXEOJDTHI-VQHPVUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 在 吡啶 、 4 A molecular sieve 、 sodium methylate 、 对甲苯磺酸 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 15.5h， 生成 (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

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.