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Synthesis of D-altritol Nucleosides With a 3'-O-tert-butyldimethylsilyl Protecting Group

Synthesis of D-altritol Nucleosides With a 3'-O-tert-butyldimethylsilyl Protecting Group

Michael Abramov, Arnaud Marchand, Agnes Calleja-Marchand, Piet Herdewijn

Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):439-55.

PMID: 15043165

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18162486	tert-Butyldimethylsilyl chloride		18162-48-6	Price

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