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Synthesis of 2-deoxy-C-glycosides via Lewis acid-mediated rearrangement of 2,3-anhydro-1-thiopyranosides
| Content Provider | Semantic Scholar |
|---|---|
| Author | Xiong, De-Cai Gao, Chao Li, Wenming Wang, Yuan Li, Qin Long Ye, Xin-Shan |
| Copyright Year | 2014 |
| Abstract | An approach to the regio- and stereo-selective construction of 2-deoxy-C-glycosides via Lewis acid-mediated rearrangement of 2,3-anhydro-1-thiopyranosides is disclosed. Treatment of 2,3-anhydro-1-thiopyranosides with phenols in the presence of TMSOTf, the migration–O-glycosylation and Fries-like O to C rearrangement took place in succession, providing aryl 2-thio-2-deoxy-C-glycosides with the single thermodynamically favourable configuration (1C4 or 4C1) in good to excellent yields. The coupling reaction of 2,3-anhydro-1-thiopyranosides with trimethylsilylated or tributylstanylated nucleophiles in the presence of TMSOTf or Sc(OTf)3, via the migration–C-glycosylation process, afforded 2-thio-2-deoxy-C-glycosides in a stereospecific manner in moderate to good yields and with the C-1 and C-2 substituents opposite. The 2-thio-functionality was further removed to produce the corresponding 2-deoxy-C-glycosides. This method may provide a convenient route for the preparation of 2-deoxy-C-glycosides. |
| Starting Page | 798 |
| Ending Page | 806 |
| Page Count | 9 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/C4QO00113C |
| Volume Number | 1 |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/qo/c4/c4qo00113c/c4qo00113c1.pdf |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/getauthorversionpdf/C4QO00113C |
| Alternate Webpage(s) | https://doi.org/10.1039/C4QO00113C |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
