((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)(furan-2-yl)methanol | 1346433-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)(furan-2-yl)methanol
• 英文别名: furan-2-yl-[(2R,3R,4S,5R)-3-[(4-methoxyphenyl)methoxy]-5-methyl-4-phenylmethoxyoxolan-2-yl]methanol
• CAS: 1346433-79-1
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: WHHYRIQBMQJZFM-LRSSEXJUSA-N

物化性质

• 沸点：
  542.7±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)(furan-2-yl)methanol 在 重铬酸吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 22.0h， 生成 (2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one
  参考文献：
  名称：

  A Carbohydrate-Based Total Syntheses of (+)-Pyrenolide D and (−)-4-epi-Pyrenolide D

  摘要：

  Efficient total syntheses of (+)-pyrenolide D (5) and (-)-4-epi-pyrenolide D (6) have been achieved from a known 5-deoxy-D-xylose derivative 9 in ten steps with 19% overall yield either exclusively as 5 or as pure 5 and 6 in a 3:2 ratio. Key steps involved are one-pot epoxidation-cyclization by Corey-Chaykvosky reagent, reductive Barton-McCombie deoxygenation, and per-acid mediated oxidative spiroketalization.

  DOI：

  10.1021/jo201570h
• 作为产物：
  描述：

  (2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol 在 正丁基锂 、 camphor-10-sulfonic acid 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 11.5h， 生成 ((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)(furan-2-yl)methanol
  参考文献：
  名称：

  A Carbohydrate-Based Total Syntheses of (+)-Pyrenolide D and (−)-4-epi-Pyrenolide D

  摘要：

  Efficient total syntheses of (+)-pyrenolide D (5) and (-)-4-epi-pyrenolide D (6) have been achieved from a known 5-deoxy-D-xylose derivative 9 in ten steps with 19% overall yield either exclusively as 5 or as pure 5 and 6 in a 3:2 ratio. Key steps involved are one-pot epoxidation-cyclization by Corey-Chaykvosky reagent, reductive Barton-McCombie deoxygenation, and per-acid mediated oxidative spiroketalization.

  DOI：

  10.1021/jo201570h

文献信息

• A Carbohydrate-Based Total Syntheses of (+)-Pyrenolide D and (−)-4-<i>epi</i>-Pyrenolide D
  作者：Barla Thirupathi、P. Purushotam Reddy、Debendra K. Mohapatra

  DOI：10.1021/jo201570h

  日期：2011.12.2

  Efficient total syntheses of (+)-pyrenolide D (5) and (-)-4-epi-pyrenolide D (6) have been achieved from a known 5-deoxy-D-xylose derivative 9 in ten steps with 19% overall yield either exclusively as 5 or as pure 5 and 6 in a 3:2 ratio. Key steps involved are one-pot epoxidation-cyclization by Corey-Chaykvosky reagent, reductive Barton-McCombie deoxygenation, and per-acid mediated oxidative spiroketalization.