(+/-)-(3R,4S,6R)-4-benzyloxy-6-benzyloxymethyl-6-methyl-3-vinyl-tetrahydropyran-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-(3R,4S,6R)-4-benzyloxy-6-benzyloxymethyl-6-methyl-3-vinyl-tetrahydropyran-3-ol
• 英文别名: (3S,4R,6S)-3-ethenyl-6-methyl-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-ol
• 化学式: C₂₃H₂₈O₄
• 分子量: 368.473
• InChiKey: GEUDLIQNIAGBGE-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-(3R,4S,6R)-4-benzyloxy-6-benzyloxymethyl-6-methyl-3-vinyl-tetrahydropyran-3-ol 在 acetylacetonatodicarbonylrhodium(l) 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氢气 、 N-甲基吗啉氧化物 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 20.0~60.0 ℃ 、2.0 MPa 条件下， 反应 20.0h， 生成 (+/-)-(5R,8R,10S)-10-benzyloxy-8-benzyloxymethyl-8-methyl-1,7-dioxaspiro[4,5]decan-2-one
  参考文献：
  名称：

  Combining Ring-Closing Metathesis and Hydroformylation Strategies:  A Novel Approach to Spirocyclic γ-Butyrolactones

  摘要：

  Di- or tetrahydropyrans with a vinyl side chain are obtained by diastereoselective ring-closing metathesis or by addition of vinylmagnesium chloride to an appropriately functionalized tetrahy-dropyranone. The resulting allylic alcohols are converted to spirocyclic hemiacetals under hydroformylation conditions. Oxidation yields the corresponding lactones.

  DOI：

  10.1021/jo0157730
• 作为产物：
  描述：

  4-benzyloxymethyl-4-methyl-3,7-dioxabicyclo[4.1.o]heptane 在 四丙基高钌酸铵 、 4 A molecular sieve 、 三氟化硼乙醚 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (+/-)-(3R,4S,6R)-4-benzyloxy-6-benzyloxymethyl-6-methyl-3-vinyl-tetrahydropyran-3-ol
  参考文献：
  名称：

  Combining Ring-Closing Metathesis and Hydroformylation Strategies:  A Novel Approach to Spirocyclic γ-Butyrolactones

  摘要：

  Di- or tetrahydropyrans with a vinyl side chain are obtained by diastereoselective ring-closing metathesis or by addition of vinylmagnesium chloride to an appropriately functionalized tetrahy-dropyranone. The resulting allylic alcohols are converted to spirocyclic hemiacetals under hydroformylation conditions. Oxidation yields the corresponding lactones.

  DOI：

  10.1021/jo0157730

文献信息

• Combining Ring-Closing Metathesis and Hydroformylation Strategies:  A Novel Approach to Spirocyclic γ-Butyrolactones
  作者：Bernd Schmidt、Burkhard Costisella、Rafael Roggenbuck、Markus Westhus、Holger Wildemann、Peter Eilbracht

  DOI：10.1021/jo0157730

  日期：2001.11.1

  Di- or tetrahydropyrans with a vinyl side chain are obtained by diastereoselective ring-closing metathesis or by addition of vinylmagnesium chloride to an appropriately functionalized tetrahy-dropyranone. The resulting allylic alcohols are converted to spirocyclic hemiacetals under hydroformylation conditions. Oxidation yields the corresponding lactones.