Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester | 290334-85-9

• 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: Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester
• 英文别名: [(2R)-2-[(4R,5R)-2,2-dimethyl-5-[(1S)-1-phenylmethoxypentyl]-1,3-dioxolan-4-yl]-2-hydroxyethyl] 4-methylbenzenesulfonate
• CAS: 290334-85-9
• 化学式: C₂₆H₃₆O₇S
• 分子量: 492.634
• InChiKey: XMXKSXVRLLDYHW-ZFFYZDHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 potassium carbonate 、 silver carbonate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 正己烷 、 苯 为溶剂， 反应 47.5h， 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
• 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 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 62.67h， 生成 Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester
  参考文献：
  名称：

  Formal total synthesis of (+)-boronolide

  摘要：

  (+) 硼诺笼，作为一种拥有四个连续手性中心的聚乙酸酯类天然产物，已从 D-甘露醇中成功合成。（C）2000 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(00)00749-8

文献信息

• Formal total synthesis of (+)-boronolide
  作者：Musti Chandrasekhar、Sushil Raina、Vinod K Singh

  DOI：10.1016/s0040-4039(00)00749-8

  日期：2000.6

  (+)-Boronolide, a polyacetoxy natural product having four contiguous asymmetric centers has been synthesized from D-mannitol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  (+) 硼诺笼，作为一种拥有四个连续手性中心的聚乙酸酯类天然产物，已从 D-甘露醇中成功合成。（C）2000 Elsevier Science Ltd. 保留所有权利。
• 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.