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Nucleoside Analogues from Push-Pull Functionalized Branched-Chain Pyranosides
| Content Provider | Semantic Scholar |
|---|---|
| Author | Kordian, Marcus Feist, Holger Kantlehner, Willi Michalik, Manfred Peseke, Klaus |
| Copyright Year | 2006 |
| Abstract | The reaction of methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose (1) with ethynylmagnesium bromide in tetrahydrofuran and subsequent trimethylsilylation yielded the methyl 4,6-O-benzylidene-2-deoxy-3-C-ethynyl-3-O-trimethylsilyl-α-D-ribo-hexopyranoside (3). Push-pull functionalization of 3 with N,N,N′,N′,N″,N″-hexamethylguanidinium chloride under basic conditions and following deprotection afforded the spiro{2,5-dihydro-3-dimethylamino- furan-2,8’-4’,4’a,6’,7’,8’,8’a-hexahydro-6’-methoxy-2’-phenyl-pyrano[3,2-d][1.3]dioxine}- 5-ylidenemalononitrile (9). Furthermore, compound 1 reacted with N,N-dimethylformamide dimethylacetal to furnish methyl (E)-4,6-O-benzylidene-2-deoxy-2-dimethylaminomethylene-α-Derythro- hexopyranosid-3-ulose (10). Treatment of 10 with methylhydrazine and amidines yielded (4S,5aR,8R,9aS)-2,5a,6,9a-tetrahydro-4-methoxy-2-methyl-8-phenyl-4H-[1,3]dioxino[4’,5’:5,6]- pyrano[4,3-c]pyrazole (11a) and (2R,4aR,6S,10bS)-4,4a,6,10b-tetrahydro-6-methoxy-2-phenyl- [1,3]dioxino[4’,5’:5,6]pyrano[4,3-d]pyrimidines 12, respectively |
| Starting Page | 406 |
| Ending Page | 412 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1515/znb-2006-0406 |
| Alternate Webpage(s) | http://www.znaturforsch.com/ab/v61b/61b0406.pdf |
| Alternate Webpage(s) | http://www.znaturforsch.com/ab/v61b/s61b0406.pdf |
| Alternate Webpage(s) | https://doi.org/10.1515/znb-2006-0406 |
| Volume Number | 61 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
