(3S,4S,5S)-(-)-5-benzyloxymethyl-3,4-dihydroxydihydro-furan-2-one | 395640-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5S)-(-)-5-benzyloxymethyl-3,4-dihydroxydihydro-furan-2-one
• 英文别名: (3S,4R,5S)-3,4-dihydroxy-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 395640-41-2
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: AJNNHEUSPPQEDM-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-(-)-5-benzyloxymethyl-3,4-dihydroxydihydro-furan-2-one 在 溴 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (4R,5S)-(-)-5-benzyloxymethyl-4-hydroxy-dihydro-furan-2-one
  参考文献：
  名称：

  A facile access to 2-deoxy-l-ribose

  摘要：

  The title compound was prepared in five steps starting from R-(+)-5-benzyloxymethyl-5H-furan-2-one 1 via syn-dihydroxylation of its double bond, regioselective tosylation of the 2-OH group in the thus obtained diol 2 followed by selective deoxygenation of that position. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00386-x
• 作为产物：
  描述：

  (+)-(R)-5-benzyloxymethylfuran-2(5H)-one 在 二环己烷并-18-冠醚-6 、 potassium permanganate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到(3S,4S,5S)-(-)-5-benzyloxymethyl-3,4-dihydroxydihydro-furan-2-one
  参考文献：
  名称：

  A facile access to 2-deoxy-l-ribose

  摘要：

  The title compound was prepared in five steps starting from R-(+)-5-benzyloxymethyl-5H-furan-2-one 1 via syn-dihydroxylation of its double bond, regioselective tosylation of the 2-OH group in the thus obtained diol 2 followed by selective deoxygenation of that position. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00386-x

文献信息

• THE STEREOSELECTIVE SYNTHESIS OF 2,3-<i>CIS</i>-DIHYDROXY-γ-BUTYROLACTONES BY THE OXIDATION OF γ-BUTENOLIDES WITH KMnO₄-CROWN ETHER
  作者：Teruaki Mukaiyama、Fujio Tabusa、Keisuke Suzuki

  DOI：10.1246/cl.1983.173

  日期：1983.2.5

  Oxidation of γ-butenolides was effected by KMnO4-crown ether to afford the corresponding 2,3-cis-dihydroxy-γ-butyrolactones in high yields. High stereoselectivity was observed in cases when bulky substituents were introduced at the γ-position of the butenolides.

  γ-丁烯醇的氧化作用由KMnO4-冠醚实现，以高产量提供相应的2,3-顺式-二羟基-γ-丁内酯。当在丁烯醇的γ位引入大体积的取代基时，观察到高立体选择性。
• A facile access to 2-deoxy-l-ribose
  作者：Fabio Fazio、Manfred P. Schneider

  DOI：10.1016/s0957-4166(01)00386-x

  日期：2001.8

  The title compound was prepared in five steps starting from R-(+)-5-benzyloxymethyl-5H-furan-2-one 1 via syn-dihydroxylation of its double bond, regioselective tosylation of the 2-OH group in the thus obtained diol 2 followed by selective deoxygenation of that position. (C) 2001 Elsevier Science Ltd. All rights reserved.