(diisopropylphosphonyl)methyl 2,3-dideoxy-β-D-glycero-pent-2-eno pyranoside | 166769-13-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (diisopropylphosphonyl)methyl 2,3-dideoxy-β-D-glycero-pent-2-eno pyranoside
• 英文别名: (3S,6S)-6-[di(propan-2-yloxy)phosphorylmethoxy]-3,6-dihydro-2H-pyran-3-ol
• CAS: 166769-13-7
• 化学式: C₁₂H₂₃O₆P
• 分子量: 294.285
• InChiKey: UEXQCZMJACCGLC-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (diisopropylphosphonyl)methyl 2,3-dideoxy-β-D-glycero-pent-2-eno pyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 ((2S,5S)-5-Hydroxy-tetrahydro-pyran-2-yloxymethyl)-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of phosphonate derivatives of tetrahydro- and dihydro-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement

  摘要：

  Phosphonate derivatives of 2,5-cis substituted tetrahydro- and dihydro-2H-pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4-trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5-cis-dihydro-2H-pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5-cis-dihydro-2H-pyranyl nucleosides.

  DOI：

  10.1016/0957-4166(95)00108-2
• 作为产物：
  描述：

  (2E,4E)-5-(4-羟基-2,2,6-三甲基-7-氧杂二环[4.1.0]庚-1-基)-3-甲基戊-2,4-二烯醛 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.33h， 生成 (diisopropylphosphonyl)methyl 2,3-dideoxy-β-D-glycero-pent-2-eno pyranoside
  参考文献：
  名称：

  Stereocontrolled synthesis of phosphonate derivatives of tetrahydro- and dihydro-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement

  摘要：

  Phosphonate derivatives of 2,5-cis substituted tetrahydro- and dihydro-2H-pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4-trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5-cis-dihydro-2H-pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5-cis-dihydro-2H-pyranyl nucleosides.

  DOI：

  10.1016/0957-4166(95)00108-2

文献信息

• Stereocontrolled synthesis of phosphonate derivatives of tetrahydro- and dihydro-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement
  作者：María-Jesús Pérez-Pérez、Bogdan Doboszewski、Jef Rozenski、Piet Herdewijn

  DOI：10.1016/0957-4166(95)00108-2

  日期：1995.4

  Phosphonate derivatives of 2,5-cis substituted tetrahydro- and dihydro-2H-pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4-trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5-cis-dihydro-2H-pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5-cis-dihydro-2H-pyranyl nucleosides.