ethyl 2-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2-ethoxy-4-phenylmethoxyoxolan-3-yl]acetate | 250369-64-3

• 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: ethyl 2-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2-ethoxy-4-phenylmethoxyoxolan-3-yl]acetate
• CAS: 250369-64-3
• 化学式: C₁₉H₂₈O₇
• 分子量: 368.427
• InChiKey: UVRWVTJTVRUUJN-GQZGXJHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2-ethoxy-4-phenylmethoxyoxolan-3-yl]acetate 在 sodium periodate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.33h， 生成 ethyl 2-[(3R,4R,5S)-5-acetyl-2-ethoxy-4-phenylmethoxyoxolan-3-yl]acetate
  参考文献：
  名称：

  Synthetic Studies on Norrisolide:  Enantioselective Synthesis of the Norrisane Side Chain

  摘要：

  [GRAPHICS]Norrisolide (1) belongs to a family of marine diterpenes that are characterized by the assembly of a bicyclic core with a unique and highly oxygenated side chain (norrisane side chain). As a prelude to the synthesis of 1, we present herein a short, efficient, and enantioselective synthesis of the norrisane side chain 4. The synthetic route toward 4 departs from D-mannose and is short (11 steps), efficient, and enantioselective.

  DOI：

  10.1021/ol9909785
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol 在 dirhodium tetraacetate 、 硫酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 ethyl 2-[(3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2-ethoxy-4-phenylmethoxyoxolan-3-yl]acetate
  参考文献：
  名称：

  Synthetic Studies on Norrisolide:  Enantioselective Synthesis of the Norrisane Side Chain

  摘要：

  [GRAPHICS]Norrisolide (1) belongs to a family of marine diterpenes that are characterized by the assembly of a bicyclic core with a unique and highly oxygenated side chain (norrisane side chain). As a prelude to the synthesis of 1, we present herein a short, efficient, and enantioselective synthesis of the norrisane side chain 4. The synthetic route toward 4 departs from D-mannose and is short (11 steps), efficient, and enantioselective.

  DOI：

  10.1021/ol9909785

文献信息

• Synthetic Studies on Norrisolide:  Enantioselective Synthesis of the Norrisane Side Chain
  作者：Charles Kim、Richard Hoang、Emmanuel A. Theodorakis

  DOI：10.1021/ol9909785

  日期：1999.10.1

  [GRAPHICS]Norrisolide (1) belongs to a family of marine diterpenes that are characterized by the assembly of a bicyclic core with a unique and highly oxygenated side chain (norrisane side chain). As a prelude to the synthesis of 1, we present herein a short, efficient, and enantioselective synthesis of the norrisane side chain 4. The synthetic route toward 4 departs from D-mannose and is short (11 steps), efficient, and enantioselective.