title: Synthesis of D-altritol nucleosides with a 3'-O-tert-butyldimethylsilyl protecting group.
abstract: 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.
authors.affiliation: Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Leuven, Belgium.
authors.forename: Michael
authors.initials: M
authors.lastname: Abramov
authors.forename: Arnaud
authors.initials: A
authors.lastname: Marchand
authors.forename: Agnes
authors.initials: A
authors.lastname: Calleja-Marchand
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D009705:Nucleosides / Q000138:chemical synthesis*; D012821:Silanes / Q000138:chemical synthesis*; D013402:Sugar Alcohols / Q000138:chemical synthesis*
chemical_list: D009705:Nucleosides; D012821:Silanes; D013402:Sugar Alcohols; C042890:altritol