2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal | 185987-56-8

• 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: 2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal
• 英文别名: (2R,3S,4R)-5-[tert-butyl(dimethyl)silyl]oxy-2,3,4-tris(phenylmethoxy)pentanal
• CAS: 185987-56-8
• 化学式: C₃₂H₄₂O₅Si
• 分子量: 534.768
• InChiKey: MJWNIMUKDVUDCS-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal 在 sodium hydroxide 、 四丁基氟化铵 、 sodium cyanoborohydride 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (3R,4R,5S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-hydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-8,10,12,14-tetramethyl-3,4,5-tris(phenylmethoxy)-1-oxa-7-azacyclopentadecan-15-one
  参考文献：
  名称：

  Chimeric Azalides with Functionalized Western Portions

  摘要：

  DOI：

  10.3987/com-96-7569
• 作为产物：
  描述：

  D-xylose diethyl dithioacetal 在 咪唑 、 四丁基碘化铵 、 sodium hydride 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 17.5h， 生成 2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d

文献信息

• Process of producing 8A- and 9A-azalide antibiotics
  申请人：Merck & Co., Inc.

  公开号：US05332807A1

  公开（公告）日：1994-07-26

  A process of producing 8a- and 9a- azalide compounds is disclosed, comprised of reacting an 8a- aza or 9a- aza azalide eastern fragment or a derivative thereof with a compound of the formula: X--A'--Y wherein X and Y are appropriate reactive groups and A' is a fragment or compound which forms the western portion of the azalide, and cyclizing this intermediate to form the target 8a- or 9a-azalide compound. Compounds of formula I, II and III as well as other azalides can be synthesized according to this process.

  披露了一种生产8a-和9a-氮杂环化合物的方法，包括将8a-氮杂或9a-氮杂氮杂环东部片段或其衍生物与以下化合物的反应：X--A'--Y，其中X和Y是适当的反应基团，A'是形成氮杂环西部的片段或化合物，然后将此中间体环化以形成目标8a-或9a-氮杂环化合物。可以根据此过程合成I、II和III型公式化合物以及其他氮杂环化合物。
• A Synthesis of (+)-Cyclophellitol from <scp>d</scp>-Xylose
  作者：Frederick E. Ziegler、Yizhe Wang

  DOI：10.1021/jo971998s

  日期：1998.2.1
• Chimeric Azalides with Functionalized Western Portions
  作者：Sherman T. Waddell、Jeffrey M. Eckert、Timothy A. Blizzard

  DOI：10.3987/com-96-7569

  日期：——
• Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol
  作者：Frederick E. Ziegler、Yizhe Wang

  DOI：10.1021/jo981211d

  日期：1998.10.1

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.