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