(2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol | 181137-83-7

• 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: (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol
• 英文别名: (1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4-methoxyphenyl)methoxy]butan-1-ol
• CAS: 181137-83-7
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: DZJRBHNCJRGKCZ-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol 在 sodium periodate 、 重铬酸吡啶 、 水 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-5-(4-Methoxy-benzyloxy)-2-((S)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butoxy)-pentanoic acid
  参考文献：
  名称：

  Clark, J. Stephen; Dossetter, Alexander G.; Blake, Alexander J., Chemical Communications, 1999, # 8, p. 749 - 750

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3-bromopropoxymethyl)-4-methoxy-benzene 、 (R)-(-)-甘油醇缩丙酮 在 magnesium 、 1,2-二溴乙烷 、 copper(l) iodide 、 二甲基硫 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以93%的产率得到(2R,3R)-1,2-O-isopropylidene-6-[(4-methoxybenzyl)oxy]hexane-1,2,3-triol
  参考文献：
  名称：

  Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid

  摘要：

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.

  DOI：

  10.1021/jo702111u

文献信息

• Synthesis of the Tricyclic Core of Labiatin A and Australin A
  作者：J. Stephen Clark、David Vignard、Andrew Parkin

  DOI：10.1021/ol201498g

  日期：2011.8.5

  diterpene natural products labiatin A and australin A has been accomplished. The key ring-forming transformation is a cascade reaction comprising generation of a copper carbenoid from a diazo ketone, intramolecular reaction of the carbenoid with a cyclic ether, and rearrangement of the resulting free oxonium ylide or its metal-bound equivalent with ring expansion of the original cyclic ether.

  海洋二萜天然产物Labiatin A和Australin A的三环核心的简明合成方法已经完成。关键的成环转化是一种级联反应，包括从重氮酮生成铜类胡萝卜素，类胡萝卜素与环醚的分子内反应以及所得游离氧代叶立德或其金属键合等价物的重排以及环的扩环。原始环醚。
• Synthesis of the Tricyclic Core of the Marine Natural Product Labiatin A
  作者：J. Stephen Clark、Carl A. Baxter、José L. Castro

  DOI：10.1055/s-2005-918485

  日期：——

  A synthetic route to a model of the tricyclic core of labiatin A is described. Two catalytic metal carbenoid reactions, C-H insertion and oxonium ylide generation with subsequent [2,3]-sigmatropic rearrangement, have been used to assemble the tricyclic system in an efficient and stereoselective manner.

  描述了获得唇形蛋白 A 三环核心模型的合成路线。两种催化金属类卡宾反应，CH 插入和氧鎓叶立德生成以及随后的 [2,3]-σ 重排，已被用于以有效和立体选择性的方式组装三环体系。
• Stereoselective synthesis of the bicyclic core structure of the highly oxidised sesquiterpene neoliacinic acid
  作者：J.Stephen Clark、Alexander G. Dossetter、William G. Whittingham

  DOI：10.1016/0040-4039(96)01136-7

  日期：1996.7

  The bicyclic core (3) of the sesquiterpene neoliacinic acid (1) has been constructed in a stereoselective manner by [2,3]-sigmatropic ring-expansion of an oxonium ylide generated catalytically from the α-diazo ketone 4.

  倍半萜新芥酸（1）的双环核（3）已通过[2,3]-σ环扩环由α-重氮酮4催化生成的氧鎓叶立德以立体选择性方式构建。
• Clark, J. Stephen; Dossetter, Alexander G.; Blake, Alexander J., Chemical Communications, 1999, # 8, p. 749 - 750
  作者：Clark, J. Stephen、Dossetter, Alexander G.、Blake, Alexander J.、Li, Wan-Sheung、Whittingham, William G.

  DOI：——

  日期：——
• Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid
  作者：J. Stephen Clark、Carl A. Baxter、Alexander G. Dossetter、Stéphane Poigny、José L. Castro、William G. Whittingham

  DOI：10.1021/jo702111u

  日期：2008.2.1

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.