((2S*,3R*)-2-benzyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-methanol

• 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: ((2S*,3R*)-2-benzyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-methanol
• 英文别名: [(2S,3R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-3-yl]methanol
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: AXULXAXCBRFOMH-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  顺-4-苄氧基-2-丁烯-1-醇 在 4-二甲氨基吡啶 、 copper(l) iodide 、 Grubbs catalyst first generation 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 ((2S*,3R*)-2-benzyloxymethyl-3,6-dihydro-2H-pyran-3-yl)-methanol
  参考文献：
  名称：

  Di- and tetrahydropyrans with orthogonally protected hydroxymethyl side chains: a synthetic route and the structure elucidation of an unexpected acetal cleavage product

  摘要：

  A synthesis of dihydropyrans with orthogonally protected hydroxymethyl side chains is presented in this contribution. Key steps of the synthesis are the regioselective epoxide opening using vinyl cuprate reagents, selective protection of primary alcohols and ring closing metathesis. A strategy based on the intermediate formation of a rigid bicyclic acetal turned out to be unsuccessful due to the unexpected formation of an annellated furanopyran rearrangement product 6. Elucidation of the structure was achieved using one- and two-dimensional NMR-methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00913-4

文献信息

• Di- and tetrahydropyrans with orthogonally protected hydroxymethyl side chains: a synthetic route and the structure elucidation of an unexpected acetal cleavage product
  作者：Bernd Schmidt、Michael Pohler、Burkhard Costisella

  DOI：10.1016/s0040-4020(02)00913-4

  日期：2002.9

  A synthesis of dihydropyrans with orthogonally protected hydroxymethyl side chains is presented in this contribution. Key steps of the synthesis are the regioselective epoxide opening using vinyl cuprate reagents, selective protection of primary alcohols and ring closing metathesis. A strategy based on the intermediate formation of a rigid bicyclic acetal turned out to be unsuccessful due to the unexpected formation of an annellated furanopyran rearrangement product 6. Elucidation of the structure was achieved using one- and two-dimensional NMR-methods. (C) 2002 Elsevier Science Ltd. All rights reserved.