3 -Azido-3 -deoxy-3-

Comparison of the -n.m.r. spectrum of 3-0-(methylsulfonyl)-/3-maltose heptaacetate (31) with that of /3-maltose octaacetate showed only one divergence, —0.34 p.p.m. upfield of the H-3 resonance, indicative of the location of the methylsulfonyloxy group on C-3. A similar comparison of H-n.m.r.-spectral parameters as between methyl 4 -0-(methylsulfonyl)-/3-maltoside hexaacetate and methyl /3-maltoside heptaacetate revealed that the methylsulfonyloxy group in the former compound is located on C-4, as the H-4 resonance appeared —0.3 p.p.m. to higher field than the H-4 resonance for the heptaacetate.66 In the H-n.m.r. spectrum of methyl 3-azido-3-deoxy-/3-maltoside heptaacetate, the H-3 resonance appeared at 1.70 p.p.m. to higher field of... 

Azido-2 -deoxyuridine 5 -triphosphate (5-N3-dUTP) has been enzymically converted by E. coli DNA polymerase (in the dark) to a photoreactive DNA which was then used to photolabel the lac repressor (230). Alternatively, when 5-N3-dUTP was irradiated in the presence of DNA polymerase, it functioned as a photoaffinity label of the enzyme (231). The syntheses of several photoreactive 3 -arylazido derivatives of ATP (232) as well as of 9-(3 -azido-3 -deoxy-/3-D-xylofuranosyl)adenosine and -guanosine 5 -triphosphates (233) have been described. 

Tronchet s group has extended its studies of the 1,3-dipolar cycloaddition of phenylacetylene to nitrile oxide derivatives of sugars to include the synthesis of 5-phenylisoxazole derivatives of 1,2-substituted 3-azido-3-deoxy-, 3-amino-3-deoxy-, and S-trifluoroacetamido-S-deoxy-a-D-xy/o-tetrofuranose, and 3-acet-amido-3-deoxy-a-D-r/6o-tetrofuranose (171). 2-Amino-2-deoxy-D-glucose reacted with substituted-phenyl thiocyanates to yield condensed imidazolidine derivatives (172), and a j/ /ro-benzimidazoline prepared from l,2 5,6-di-(9-... 

M. Kloostennan, M. P. de Nijs, and I. H. van Boom, Synthesis of 1,6-anhydro-2-0-trifluoro-methanesulphonyl-B-D-mannopyranose derivatives and their conversion into the corresponding 1,6-anhydro-2-azido-deoxy-p-D-giucopyranoses A convenient and efficient approach, J. Car-bohydr. Qum. 5 215 (1986). 

Bozo, E, Boros, S, Kuszmann, J, Synthesis of 4-cyanophenyl 4-azido -deoxy-l,5-dithio-p-D-xylopyranoside, Carbohydr. Res., 302, 149-162, 1997. 

From study of the action of invertase on derivatives of sucrose and methyl jS-D-fructofuranoside, it was concluded that small changes at positions 1, or 6 cause loss of enzymic acitivity various azido-, deoxy, and halogenated-derivatives were examined. " ... 

Treatment of methyl 2-azido-4,6-0-benzylidene-2-deoxy-a-D-altro-pyranoside (128) (42) with 121 followed by refluxing and processing afforded a chloro derivative as a sirup in 70% yield (46, 49). Reduction of this product with an excess of Raney-nickel in methanol containing acetic anhydride afforded a crystalline product, m.p. 179°C., which is formulated as the d-manno analog 131. The actual product is most likely methyl azido-4,6-0-benzylidene-3-chloro-2,3-dideodxy - a - d - mannopyran-oside (130) resulting from attack of chloride ion at C-3 with inversion of configuration in the intermediate 129. Had the chlorination proceeded... 

Deoxy-6-iodo-a-D-fructofuranose p-D-fructopyranose 1,2 2,1 -dianhydride (49) 6-Chloro-6-deoxy-a-D-fructofuranose p-D-fructopyranose 1,2 2,1 -dianhydride (50) 6-5-Heptyl-6-thio-tt-D-fructofuranose p-D-fructopyranose 1,2 2,l -dianhydride (51) 6-Azido-6-deoxy-a-D-ffuctofuranose P-D-fructopyranose 1,2 2,l -dianhydride (52) 6-Anuno-6-deoxy-a-D-fructofuranose p-D-fructopyranose 1,2 2,l -dianhydride (53) 6-Acetamido-6-deoxy-a-D-fructofuranose p-D-fructopyranose 1,2 2,l -dianhydride (54)... 

The Mukaiyama condensation method was also utilized in the synthesis of several antibiotics and related bioactive substances. These syntheses include apramycin, using 4-azido-2,3,6-tri-(P-benzyl-4-deoxy-) -D-glucopyranosyl fluoride (prepared from the corresponding a-D-glucopyranosyl chloride by the AgF method ) avermectin B , using protected sugar derivatives of oleandrosyl fluoride (a-L-Ole-F) and 0-(a-L-01e)-(1 4)-a-L-0le-F (both... 

Treatment of the 2-triflate (224) of methyl 3-azido-4,6-0-benzylidene-3-deoxy-a-D-idopyranoside with BU4NF (DMF, r.t.) readily gave the... 

O-benzylidene-, benzyl ester N-(benzyloxycarbonyl)-, benzyl ester N-(benzyloxycarbonyl)-, methyl ester 2-azido-2-deoxy, N-(benzyloxycarbonyl)-benzyl ester methyl ester... 

Huang P, Farquhar D, Plunkett W. Selective action of 3 -azido-3 -deoxy-thymidine 5 -triphosphate on viral reverse transcriptases and human DNA polymerases. J Biol Chem 1990 265 11914-11918. 

Yao, S. Y., C. E. Cass, and J. D. Young. Transport of the antiviral nucleoside analogs 3 -azido-3 -deoxy-fhymidine and 2, 3 -dideoxycytidine by a recombinant nucleoside transporter (rCNT) expressed in Xenopus laevis oocytes. Mol. Pharmacol. 1996, 50, 388-393. 

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