(6R)-6-((4R,5R)-5-((S)-1-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydro-2H-pyran-2-one | 540727-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (6R)-6-((4R,5R)-5-((S)-1-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydro-2H-pyran-2-one
• 英文别名: 6-[5-(1-hydroxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]tetrahydropyran-2-one；(6R)-6-[(4R,5R)-5-[(1S)-1-hydroxypentyl]-2,2-dimethyl-1,3-dioxolan-4-yl]oxan-2-one
• CAS: 540727-84-2
• 化学式: C₁₅H₂₆O₅
• 分子量: 286.368
• InChiKey: CKNQSIPXYYJOGF-OIMNJJJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R)-6-((4R,5R)-5-((S)-1-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydro-2H-pyran-2-one 在 吡啶 、 4-二甲氨基吡啶 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 33.75h， 生成 (+)-dideacetylboronolide
  参考文献：
  名称：

  Total Synthesis of (+)-Boronolide, (+)-Deacetylboronolide, and (+)-Dideacetylboronolide

  摘要：

  Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular S(N)2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.

  DOI：

  10.1021/jo0269058
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-D-mannitol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 110.67h， 生成 (6R)-6-((4R,5R)-5-((S)-1-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (+)-Boronolide, (+)-Deacetylboronolide, and (+)-Dideacetylboronolide

  摘要：

  Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular S(N)2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.

  DOI：

  10.1021/jo0269058

文献信息

• Stereoselective synthesis of (+)-boronolide and (−)-5-epi-boronolide
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2006.03.028

  日期：2006.4

  Stereoselective synthesis of boronolide and 5-epi-boronolide was achieved from d-(−)-tartaric acid. The key step involves the reduction of a keto Weinreb amide for the synthesis of boronolide, and a single pot construction of a diketone from the bis-Weinreb amide of tartaric acid and subsequent reduction with L-Selectride for 5-epi-boronolide.

  由d-（-）-酒石酸实现了硼烷内酯和5-表-硼烷内酯的立体选择性合成。关键步骤包括还原用于合成硼烷内酯的酮威因雷伯酰胺，以及由酒石酸的双-Weinreb酰胺单锅构建二酮，随后用L-Selectride还原5-表-硼烷内酯。
• Total Synthesis of (+)-Boronolide, (+)-Deacetylboronolide, and (+)-Dideacetylboronolide
  作者：M. Chandrasekhar、Kusum L. Chandra、Vinod K. Singh

  DOI：10.1021/jo0269058

  日期：2003.5.1

  Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular S(N)2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.