(2R,3R,4aR,8aS)-3-(benzyloxy)-2-vinyloctahydropyrano[3,2-b]pyran | 1456888-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4aR,8aS)-3-(benzyloxy)-2-vinyloctahydropyrano[3,2-b]pyran
• 英文别名: 3-benzyloxy-2-vinyloctahydropyrano[3,2-b]pyran；(2R,3R,4aR,8aS)-2-ethenyl-3-phenylmethoxy-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran
• CAS: 1456888-97-3
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: DAHNLIDGSPLVKA-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-1-((2R,3S)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-3-(trimethylsilyl)penta-3,4-dien-2-ol 在 甲醇 、 四丁基氟化铵 、 sodium methylate 、 silver perchlorate 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.0h， 生成 (2R,3R,4aR,8aS)-3-(benzyloxy)-2-vinyloctahydropyrano[3,2-b]pyran
  参考文献：
  名称：

  Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes

  摘要：

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.026

文献信息

• Stereoselective Construction of Polyether trans-Pyran Ring System by Gold(I)-Catalyzed Cyclization
  作者：Hajime Yokoyama、Megumi Matsuo、Masahiro Miyazawa、Yoshiro Hirai

  DOI：10.1055/s-0035-1562525

  日期：——

  natural polyether toxins contain the trans-pyran ladder structure. We describe a synthesis of the polyether trans-pyran ring system by using cationic gold(I)-catalyzed cyclization. This gold(I)-catalyzed cyclization provided high diastereoselectivity and high turnover. This method is expected to be applicable to the synthesis of polyethers.

  许多天然聚醚毒素含有反式吡喃梯形结构。我们描述了使用阳离子金 (I) 催化环化合成聚醚反式吡喃环系统。这种金（I）催化的环化提供了高非对映选择性和高周转率。该方法有望应用于聚醚的合成。
• Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes
  作者：Yumie Suzuki、Ayano Kuwabara、Yasuhiro Koizumi、Yuji Mori

  DOI：10.1016/j.tet.2013.08.026

  日期：2013.10

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.