2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal | 116384-32-8

• 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: 2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal
• 英文别名: (2S,3S,4R)-5,5-bis(ethylsulfanyl)-2,3,4-tris(phenylmethoxy)pentanal
• CAS: 116384-32-8
• 化学式: C₃₀H₃₆O₄S₂
• 分子量: 524.745
• InChiKey: FGUCNRBAOTVTOW-SSBOKUKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 无水碳酸镉 作用下， 以 正己烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 3.67h， 生成 2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose
  参考文献：
  名称：

  Cycloaddition reactions of carbohydrate derivatives. Part 8: Intramolecular cycloaddition of nitrilimines derived from sugars

  摘要：

  Nitrilimines containing a carbon-carbon double bond were prepared in several steps from 3,3,4-tri-O-benzyl-D-xylose, D-ribose and L-arabinose derivatives and their intramolecular 1,3-dipolar cycloaddition reactions were studied. The results were examined with molecular modelling and compared with the literature data for similar cycloadditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00050-7
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal 在 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以4.6 g的产率得到2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal
  参考文献：
  名称：

  共生杀菌素C1'-C25'片段的立体选择性合成和绝对构型

  摘要：

  已经完成了共生双杀菌素的C1'-C25'片段的立体选择性合成，该共生双杀菌素是通过碱水解从共生双杀菌素的降解产物中获得的。在侧链的引入中，合成路线的特征是Kotsuki偶联和Julia-Kocienski烯烃化。该对映和立体选择性合成已经建立了C1'-C25'片段的绝对构型。

  DOI：

  10.1021/jo901162v

文献信息

• Cycloaddition reactions of carbohydrate derivatives. Part V. A hetero Diels-Alder approach to swainsonine analogs
  作者：Pál Herczegh、Imre Kovács、László Szilágyi、Ferenc Sztaricskai、Amaya Berecibar、Claude Riche、Angèle Chiaroni、Alain Olesker、Gabor Lukacs

  DOI：10.1016/s0040-4020(01)85680-5

  日期：1994.1

  Diastereoselective hetero Diels-Alder reactions of sugar derived azomethines 4a–4g have been used for the construction of chiral piperidones 6 and 7. Configuration of the major products was 6,1′-threo in every case. The enone system of 6 and 7 was reduced diastereoselectively and subsequently swainsonine-analog hydroxyindolizidines 28–32 were prepared by an intramolecular reductive amination.

  糖衍生的偶氮甲碱4a-4g的非对映选择性杂Diels-Alder反应已用于构建手性哌啶酮6和7。在每种情况下，主要产品的构型均为6,1'-苏式。非对映选择性还原6和7的烯酮体系，随后通过分子内还原胺化制备swainsonine-analog hydroxyindolizidines 28-32。
• Intramolecular reactions of compounds derived from sugars. Part II.1 Stereo-controlled intramolecular diels-alder cyclizations of 16(E,Z),8-nonatrienes and 1-AZA-6(E,Z),8-nonatrienes
  作者：Pál Herczegh、Martina Zsély、László Szilágyi、Gyula Batta、István Bajza、Rezső Bognár

  DOI：10.1016/s0040-4020(01)80109-5

  日期：1989.1

  Intramolecular Diels-Alder reactions of E,Z mixtures of nonatrienes 6 and 9 led to the exclusive formation of the bicyclic compounds 10 and 11 respectively.

  壬基6和9的E，Z混合物的分子内Diels-Alder反应分别导致双环化合物10和11的排他性形成。
• Cycloaddition reactions of carbohydrate derivatives. Part IV. Synthesis of a tetrahydroxyindolizidine through a cyclic nitrone prepared from D-xylose.
  作者：Pál Herczegh、Imre Kovács、László Szilágyi、Tamás Varga、Zoltán Dinya、Ferenc Sztaricskai

  DOI：10.1016/s0040-4039(00)77531-9

  日期：1993.2

  Intramolecular conjugate addition of the oxime from aldehyde 5 led to the formation of cyclic nitrone 6. 1,3-Dipolar cycloaddition of the latter with methyl acrylate gave the bicyclic 7 with high diastereoselection. Subsequent four-step transformation of 7 resulted in the tetrahydroxyindolizidine derivative 11.

  从醛5中肟的分子内共轭加成导致形成环硝酮6。后者与丙烯酸甲酯的1，3-偶极环加成得到具有高非对映选择性的双环7。随后的四步转化7导致四羟基吲哚并咪唑衍生物11。
• Complete stereoselectivity in the intramolecular diels-alder reactionof a triene derivative from d-xylose
  作者：Pál Herczegh、Martina Zsély、László Szilágyi、Rezső Bognár

  DOI：10.1016/s0040-4039(00)80127-6

  日期：1988.1
• 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.