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Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes
Zhang, Jingjing1; Niu, Youhong1,2; Cao, Xiaoping2; Ye, Xin-Shan1
关键词Tetrahydrothiopyrans Thiepanes Thiosugars Cycloalkenes Ramberg-backlund Reaction
刊名TETRAHEDRON
2012-06-03
DOI10.1016/j.tet.2012.03.086
68期:22页:4242-4247
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]POTENTIAL IMMUNOSUPPRESSIVE AGENTS ; POSSESSING ANTITHROMBOTIC ACTIVITY ; IMMUNODEFICIENCY-VIRUS TYPE-1 ; RING-CLOSING METATHESIS ; GLYCOSIDASE INHIBITORS ; MANNOSTATIN-A ; IMINOSUGAR DERIVATIVES ; ALDITOLS ; PRECURSORS ; CATALYSIS
英文摘要

A convenient synthesis of polyoxygenated tetrahydrothiopyrans and thiepanes from various alditol derivatives with xylo, ribo, manno, gluco, galacto, and fuco configurations is described. The preparation started from the corresponding partially protected alditols and proceeded in a ′one-pot′ manner to afford the final products in 80%-95% yield. Furthermore, thiosugar compounds 2b, 2d, and 2g were converted to the optically pure polyoxygenated cycloalkenes through Ramberg-Backlund reaction in moderate to good overall yield. The procedures can be used for the preparation of polyoxygenated thiosugars and cycloalkenes on a relatively large scale. (C) 2012 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000304295000018
项目编号21072014 ; 2012CB822100
资助机构National Natural Science Foundation of China ; Ministry of Science and Technology of China
引用统计
被引频次:9[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/54616
专题北京大学药学院
北京大学药学院_天然药物与仿生药物国家重点实验室
北京大学药学院_药物化学系
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
推荐引用方式
GB/T 7714
Zhang, Jingjing,Niu, Youhong,Cao, Xiaoping,et al. Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes[J]. TETRAHEDRON,2012,68(22):4242-4247.
APA Zhang, Jingjing,Niu, Youhong,Cao, Xiaoping,&Ye, Xin-Shan.(2012).Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes.TETRAHEDRON,68(22),4242-4247.
MLA Zhang, Jingjing,et al."Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes".TETRAHEDRON 68.22(2012):4242-4247.
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