(2S,4R)-3,4,5-tri(benzoyloxy)-6-benzyloxymethyl-3,4-dehydro-2H-pyran | 17187-67-6

• 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,4R)-3,4,5-tri(benzoyloxy)-6-benzyloxymethyl-3,4-dehydro-2H-pyran
• 英文别名: [(3S,4R)-3,4,5-tribenzoyloxy-3,4-dihydro-2H-pyran-6-yl]methyl benzoate
• CAS: 17187-67-6
• 化学式: C₃₄H₂₆O₉
• 分子量: 578.575
• InChiKey: UXFQNBYYBQNAAM-MFMCTBQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,4R)-3,4,5-tri(benzoyloxy)-6-benzyloxymethyl-3,4-dehydro-2H-pyran 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以65%的产率得到(2S,5R)-3,5-bis(benzoyloxy)-2-benzyloxymethyl-5,6-dihydro-2H-pyran
  参考文献：
  名称：

  d-Fructose- and l-sorbose-derived endo- and exo-hydroxyglycal esters and some of their chemistry

  摘要：

  Dehydrobrominations of benzoylated beta-D-fructopyranosyl and alpha-L-sorbo-pyranosyl bromides have been examined to obtain suitable conditions for effecting the elimination toward the exo- as well as the endo-positions. In the fructose case, exposure to DBU in acetonitrile generates the exo-hydroxyfructal ester (81%) while refluxing in xylene gives the endo analog (53%). In the L-sorbose case, the regioselectivities are the inverse. Simple reactions of exo- and endo-products provide a series of highly versatile enantiopure six-carbon building blocks, together with a crystalline derivative of the fungal metabolite microthecin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.018
• 作为产物：
  描述：

  1,3,4,6-tetra-O-benzoyl-α-L-sorbopyranosyl bromide 在 sodium iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸羟胺 作用下， 以 丙酮 、 吡啶 为溶剂， 反应 63.0h， 以54%的产率得到(2S,4R)-3,4,5-tri(benzoyloxy)-6-benzyloxymethyl-3,4-dehydro-2H-pyran
  参考文献：
  名称：

  d-Fructose- and l-sorbose-derived endo- and exo-hydroxyglycal esters and some of their chemistry

  摘要：

  Dehydrobrominations of benzoylated beta-D-fructopyranosyl and alpha-L-sorbo-pyranosyl bromides have been examined to obtain suitable conditions for effecting the elimination toward the exo- as well as the endo-positions. In the fructose case, exposure to DBU in acetonitrile generates the exo-hydroxyfructal ester (81%) while refluxing in xylene gives the endo analog (53%). In the L-sorbose case, the regioselectivities are the inverse. Simple reactions of exo- and endo-products provide a series of highly versatile enantiopure six-carbon building blocks, together with a crystalline derivative of the fungal metabolite microthecin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.018

文献信息

• d-Fructose- and l-sorbose-derived endo- and exo-hydroxyglycal esters and some of their chemistry
  作者：Andrea Boettcher、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2004.07.018

  日期：2004.9

  Dehydrobrominations of benzoylated beta-D-fructopyranosyl and alpha-L-sorbo-pyranosyl bromides have been examined to obtain suitable conditions for effecting the elimination toward the exo- as well as the endo-positions. In the fructose case, exposure to DBU in acetonitrile generates the exo-hydroxyfructal ester (81%) while refluxing in xylene gives the endo analog (53%). In the L-sorbose case, the regioselectivities are the inverse. Simple reactions of exo- and endo-products provide a series of highly versatile enantiopure six-carbon building blocks, together with a crystalline derivative of the fungal metabolite microthecin. (C) 2004 Elsevier Ltd. All rights reserved.