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.

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

Keywords:

• D‐altritol nucleosides
• 3′‐O‐tert‐butyldimethylsilyl protecting group
• 1,5:2,3‐dianhydro‐4,6‐O‐benzylidene‐D‐allitol

Acknowledgments

This research was financially supported by grants from the Katholicke Universiteit Leuven (GOA 2002/13) and IWT (GBOU). We thank C. Biernaux for editorial help.

Notes

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.