Deoxy sugars 2,3-dideoxy-nucleoside

Treatment of 5-deoxy-5-halogeno nucleosides of adenine and uracil with trimethylamine yielded the corresponding 5-deoxy-5-trimethylammonium salts, whose interaction with anionic polynucleotides was then examined. Various A -alkyl, A -cycloalkyl, and iV-alkaryl derivatives of 3-amino-3-deoxy-and 3, 5 -diamino-3, 5 -dideoxy-adenosine have been prepared from the amino-sugar nucleosides the 3 -benzylamino derivative gave the unusual oxazolidine derivative (52). ° ... 

Azido-5 -deoxy-nucleosides auid 5 -azido-2, 5 -dideoxy nucleosides have been prepared by a polymer support method, using polystyrenesulphonyl chloride reagent in conjunction with lithium azide,which on triphenylphosphine reduction yielded the corresponding amino-sugar nucleosides. ... 

Step procedure in 38% overall yield from adenosine (see Chaper 19, ref. 69) the sequence modifies an ethyl orthoacetate procedure described earlier by J.Engels outlined in Scheme 3, which yielded 3 -deoxy and 2, 3 -dideoxy derivatives of N-benzoyladenosine. 4-Deoxy-3-DL-erythro- and threo-pentopyranosyl pyrimidine nucleosides (16) have been synthesized using the appropriate sugar 1,2-... 

Addition of hydrazoic acid to the D-ribose derived enal (25) led to a mixture of epimeric azides (26) which were separately converted into N-benzoyl-L-ristosamine (27) and /V-benzoyl-L-acosamine (28) (Scheme 8). 2,3-Dideoxy-3-amino-nucleosides synthesized from a sugar enal derivative, are covered in Chapter 20. The 5-amino-5-deoxy-L-taluronic acid derivative (30) was obtained by addition of succinimide anion to the nitro-olefin (29) followed by ozonolysis, whereas the D-allo-derivative (31) was obtained when the nucleophile was a sulphonamide anion (Scheme 9). ... 

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