(3S,4R,5R)-4-benzyloxy-2-(hydroxymethyl)-5-methyltetrahydrofuran-3-ol | 1346433-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R)-4-benzyloxy-2-(hydroxymethyl)-5-methyltetrahydrofuran-3-ol
• 英文别名: (3S,4R,5R)-2-(hydroxymethyl)-5-methyl-4-phenylmethoxyoxolan-3-ol
• CAS: 1346433-75-7
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: VASDGIHEGHXZKK-AYDREVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-4-benzyloxy-2-(hydroxymethyl)-5-methyltetrahydrofuran-3-ol 在 咪唑 、 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 12.5h， 生成 O-[furan-2-yl-[(2S,3R,4S,5R)-3-[(4-methoxyphenyl)methoxy]-5-methyl-4-phenylmethoxyoxolan-2-yl]methyl] methylsulfanylmethanethioate
  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：

  (3R,4R,5R)-4-(benzyloxy)-5-methyltetrahydro-2,3-furandiol 、 三甲基碘化亚砜 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以65%的产率得到(3S,4R,5R)-4-benzyloxy-2-(hydroxymethyl)-5-methyltetrahydrofuran-3-ol
  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.