A base-labile protecting group (fluorenylmethoxycarbonyl) for the 5'-hydroxy function of nucleosides.
Many popular synthesis strategies look for appropriate 2'-O-protection methods to use in conjunction with 5'-O-trityl chemistry. In contrast, this unit describes the use of FMOC as a 5'-protecting group in conjunction with a ketal-type 2'-O-protecting group, 4-methoxytetrahydropyran-4-yl (MTHP). The synthesis of all four 2'-O-MTHP-5'-O-FMOC-protected ribonucleosides and 5'-O-FMOC-2'-deoxythymidine is described, as is the preparation of the N-protected, 2'-O-MTHP-protected starting nucleosides.
Gait
M J
MJ
MRC Laboratory of Molecular Biology, Cambridge, UK.
Lehmann
C
C
D000215:Acylation; D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D001671:Biochemistry / Q000379:methods*; D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
C496789:9-fluorenylmethoxycarbonyl; D005449:Fluorenes; D009705:Nucleosides; D011714:Pyrans; D012263:Ribonucleosides; D006151:Guanosine; D017665:Hydroxyl Radical; D003562:Cytidine; D000241:Adenosine; D014529:Uridine