3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol | 540727-82-0

• 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: 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol
• 英文别名: (1R)-3-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-1-phenylmethoxypentyl]-1,3-dioxolan-4-yl]pentan-1-ol
• CAS: 540727-82-0
• 化学式: C₃₄H₅₄O₇SSi
• 分子量: 634.95
• InChiKey: JHTKBBLLRFETCV-WZTFQWEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以95%的产率得到(1R)-3-(benzenesulfonyl)-1-[(4R,5R)-2,2-dimethyl-5-[(1S)-1-phenylmethoxypentyl]-1,3-dioxolan-4-yl]pentane-1,5-diol
  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 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 77.67h， 生成 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol
  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

• 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.