Four D-altritol nucleosides with a 3'-O-tert-butyldimethylsilyl protecting group are synthesized (base moieties are adenine, guanine, thymine and 5-methylcytosine). The nucleosides are obtained by ring opening reaction of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol. Optimal reaction circumstances (NaH, LiH, DBU, phase transfer, microwave irridation) for the introduction of the heterocycles are base-specific. For the introduction of the 3'-O-silyl protecting group, long reaction times and several equivalents of tert-butyldimethylsilyl chloride are needed.
Nucleic acidsNucleic acids U 0700
Synthesis of D-Altritol Nucleosides with a 3'-O-tert-Butyldimethylsilyl ProtectingGroup. -Four protected D-altritol derivatives such as (X) are prepared via an epoxide ring opening reaction as the key step. -(ABRAMOV, M.; MARCHAND, A.; CALLEJA-MARCHAND, A.; HERDEWIJN*, P.; Nucleosides, Nucleotides Nucleic
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