acetic acid 1-[2,2-dimethyl-5-(6-oxo-3,6-dihydro-2H-pyran-2-yl)[1,3]dioxolan-4-yl]pentyl ester | 263711-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: acetic acid 1-[2,2-dimethyl-5-(6-oxo-3,6-dihydro-2H-pyran-2-yl)[1,3]dioxolan-4-yl]pentyl ester
• 英文别名: [(1S)-1-[(4R,5R)-2,2-dimethyl-5-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-1,3-dioxolan-4-yl]pentyl] acetate
• CAS: 263711-16-6
• 化学式: C₁₇H₂₆O₆
• 分子量: 326.39
• InChiKey: RVEFWCAZEHSVND-SJXGUFTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acetic acid 1-[2,2-dimethyl-5-(6-oxo-3,6-dihydro-2H-pyran-2-yl)[1,3]dioxolan-4-yl]pentyl ester 在 CuCl₂*2H₂O 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以88%的产率得到(+)-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 、 copper(I) bromide dimethylsulfide complex 、 dimethyl sulfide borane 、 氢气 、 双氧水 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 silver carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 109.92h， 生成 acetic acid 1-[2,2-dimethyl-5-(6-oxo-3,6-dihydro-2H-pyran-2-yl)[1,3]dioxolan-4-yl]pentyl ester
  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

• A stereoselective synthesis of (+)-boronolide
  作者：Arun K Ghosh、Geoffrey Bilcer

  DOI：10.1016/s0040-4039(99)02246-7

  日期：2000.2

  A stereoselective synthesis of (+)-boronolide is described. The key steps involve a stereoselective reduction of an oc-hydroxy ketone, allylation of an alpha-hydroxy aldehyde and a ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester utilizing Grubbs' catalyst. (C) 2000 Elsevier Science Ltd. All rights reserved.