3,4-Di-O-benzyl-2,5,6-trideoxy-D-threo-hex-5-enose | 260265-64-3

• 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: 3,4-Di-O-benzyl-2,5,6-trideoxy-D-threo-hex-5-enose
• 英文别名: (3R,4R)-3,4-bis(phenylmethoxy)hex-5-enal
• CAS: 260265-64-3
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: HOLOEROQZVUDSK-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Di-O-benzyl-2,5,6-trideoxy-D-threo-hex-5-enose 在 salcomine 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 氧气 、 sodium iodide 作用下， 以 六甲基磷酰三胺 、 乙醇 为溶剂， 反应 6.0h， 生成 (1R,2R,3R)-1,2-dibenzyloxy-3-hydroxymethylcyclopentane
  参考文献：
  名称：

  A New Synthesis of Carbapentofuranoses from Carbohydrates

  摘要：

  Carbafuranosides were synthesized in one step from various O-protected 1,2,6-trideoxydiodo-hex-1-enitols by cobalt catalyzed 5-exo radical-cyclization under molecular oxygen. Yields were fair to good with interesting selectivities. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01395-6
• 作为产物：
  描述：

  methyl 3,4-di-O-benzyl-2,6-dideoxy-α-D-glucopyranoside 在 锌 作用下， 以 乙醇 为溶剂， 生成 3,4-Di-O-benzyl-2,5,6-trideoxy-D-threo-hex-5-enose
  参考文献：
  名称：

  立体选择性SmI 2介导的碳水化合物向环戊醇的转化

  摘要：

  碳水化合物衍生物被用作合成立体确定的环戊醇的前体。这种快速转化是通过锌辅助的Grob片段化，然后进行立体控制的SmI 2介导的环化作用来实现的。

  DOI：

  10.1016/0040-4039(95)02380-1

文献信息

• Stereocontrolled synthesis of polyhydroxylated hexahydro-1H-cyclopent[c]isoxazoles by intramolecular oxime olefin cycloadditions: an approach to aminocyclopentitols
  作者：Paul J. Dransfield、Stéphane Moutel、Michael Shipman、Vladimir Sik

  DOI：10.1039/a905706d

  日期：——

  to the newly formed hexahydro-1H-cyclopent[c]isoxazole ring system. The role of the solvent polarity on the diastereochemical outcome of these reactions is briefly discussed. Unsuccessful efforts to extend this chemistry to oximes derived from alk-4-enyl aldehydes are also presented. Finally, it is demonstrated that the hexahydro-1H-cyclopent[c]isoxazoles can be transformed into stereochemically defined

  可以将衍生自各种碳水化合物（D-葡萄糖，D-甘露糖，D-半乳糖，D-葡萄糖）的一系列烷基-5-烯基醛转化为相应的肟。这些肟的热解导致通过分子内肟烯烃环加成以良好的产率分离六氢-1 H-环戊[ c ]异恶唑。在这些环加成反应中观察到中等至优异的非对映异构控制水平，这取决于肟前体的精确性质。在最佳情况下，D-葡萄糖衍生的肟4产生六氢-1 H-环戊[ c以]异恶唑5为唯一产品​​的定量收率。观察到当肟具有与肟碳原子相邻的取代基（OBn或OBz）时，反应显示出优先产生非对映体环加合物的趋势，其中该取代基相对于新形成的hexahydro-1 H处于exo取向-环戊[ c ]异恶唑环系统。简要讨论了溶剂极性对这些反应的非对映化学结果的作用。还提出了未能成功地将这种化学方法扩展到衍生自烷基-4-烯基醛的肟的努力。最后，证明了六氢-1 H-环戊[ c可以将]异恶唑转化为立体化学定义的氨基环戊糖醇。
• Stereoselective and regioselective one-pot synthesis of polyhydroxy bicyclic diazenes and hydrazones from methyl 6-deoxy-6-iodo-hexosides
  作者：Yunfeng Li、Yao Meng、Zhongjun Li、Xiangbao Meng

  DOI：10.1016/j.tet.2015.05.105

  日期：2015.8

  An efficient, stereoselective, and base-controlled procedure for the preparation of polyhydroxy bicyclic diazenes and polyhydroxy bicyclic hydrazones is described, starting from sugar-derived methyl 6-deoxy6-iodo-hexosides. The one-pot synthesis involves a three-step reaction, including ring-opening, condensation with tosylhydrazine, and intramolecular cycloaddition with terminal alkene, which affords important synthetic precursors of bicyclic diazenes and hydrazones. (C) 2015 Elsevier Ltd. All rights reserved.
• A New Synthesis of Carbapentofuranoses from Carbohydrates
  作者：Jérôme Désiré、Jacques Prandi

  DOI：10.1016/s0040-4039(97)01395-6

  日期：1997.9

  Carbafuranosides were synthesized in one step from various O-protected 1,2,6-trideoxydiodo-hex-1-enitols by cobalt catalyzed 5-exo radical-cyclization under molecular oxygen. Yields were fair to good with interesting selectivities. (C) 1997 Elsevier Science Ltd.
• Stereoselective SmI2-mediated conversion of carbohydrates into cyclopentanols
  作者：J.J. CronjéGrové、Cedric W. Holzapfel、D.Bradley G. Williams

  DOI：10.1016/0040-4039(95)02380-1

  日期：1996.2

  Carbohydrate derivatives were employed as precursors in the synthesis of stereodefined cyclopentanols. This rapid conversion was effected by a zinc-assisted Grob-fragmentation, followed by a stereocontrolled SmI2-mediated cyclisation.

  碳水化合物衍生物被用作合成立体确定的环戊醇的前体。这种快速转化是通过锌辅助的Grob片段化，然后进行立体控制的SmI 2介导的环化作用来实现的。