(2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran | 190188-72-8

• 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: (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran
• CAS: 190188-72-8
• 化学式: C₂₇H₃₆O₄
• 分子量: 424.58
• InChiKey: PMODSLSFEOLFHZ-QEGGNFSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  三苯基氯甲烷 、 (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran 在 2,4,6-三甲基吡啶 、 盐酸 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 生成 (2R,3S)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-trityloxy-tetrahydro-pyran
  参考文献：
  名称：

  C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

  摘要：

  The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-, 1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyi-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs, the non-pyranoside substrates, but the selectivity in both cases was low. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00282-2
• 作为产物：
  描述：

  t-butyl 2,3-dideoxy-α-D-gluco-pyranoside 在 吡啶 、 selenium(IV) oxide 、 四甲基乙二胺 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 110.25h， 生成 (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran
  参考文献：
  名称：

  C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

  摘要：

  The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-, 1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyi-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs, the non-pyranoside substrates, but the selectivity in both cases was low. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00282-2