From Azido-sugars

J. Kovacs, I. Pinter, F. Szego, G. Toth, and A. Messmer, Phosphinimine derivatives of the aldopyranoses from azido sugars, Acta Chim. Acad. Sci. Hung., 101 (1979) 7-16. 

Palladium-carbon-silica Aza-from azido-sugars Reductive rearrangement... 

Oxidation is a general method for the preparation of nitro sugars from other sugar derivatives, as amino or azido sugars and sugar oximes. 

Guthrie and Irvine35 also developed an original synthesis of unsaturated isothiocyanates, starting from a mixture of the unsaturated azido sugars 15... 

D. C. Baker and D. Horton, Photolysis of azido sugar derivatives. Generation of aldehydes from 5 -azido derivatives of adenoside and uridine, Carbohydr. Res., 21 (1972) 393 105. 

Azido-sugar derivatives such as 51 were synthesized conventionally from the known trichloroethylidene carbamate derivatives such as 52, prepared by a one-pot acetalation-epimerization procedure from methyl a-D-mannopyrano-side (see Section 2.1) The 2,6-anhydro-5-azido-2-C-hydroxymethyl-L-allohep-tose derivative 53 has been synthesized from a racemic norbornenone derivative. 6-Azido-6-deoxy-, and 5,6-diazido-, 5-azido-6-fluoro- and 6-azido-5-fluoro-5,6-dideoxy-D-fructoses 54 have been prepared by polyol dehydrogenase-catalysed isomerization of the corresponding D-glucose derivatives. ... 

Full details of the synthesis of 6-azido-l,6-dideoxynojirimydn41 (see Vol 28, p. 227, ref. 52) from 1-amino-1-deoxy-D-glucitol via the intermediate azido sugar 40 have been reported together with its conversion to various analogues 42 of DNJ, and the bicyclic iminosugars castanospermine and kifunensine. ... 

A number of purine 2 -amino-2 -deoxy-8-D-ribonuc1eosides have been prepared by microbial transglycosy1 ation between the purine base and 2 -amino-2 -deoxyuridine. The 3 -azido-3 -deoxy-6- and 3 -azido,2, 3 -dideoxy-a- and 3-D-ribofuranosides of benzimidazole were synthesized conventionally from 3-azido sugar derivatives. 

Several papers have described the preparation of azido-sugars by Sj 2 displacement reactions with azide anions. Starting from 1,2-0-isopropylidene-Oi-D-xylo-furanose, Ozols et have used this method for the prearation of 3, 5 -... 

The starting material was effectively the 3-azido sugar (113) which was readily prepared from the bis-cyclohexylidene ketone (112) [cf, (23), Scheme 1] in four simple steps. Three standard operations afford the key... 

Azido-sugars are frequently prepared by reaction of epoxides with azide ion. 3-Azido-3-deoxy-L-threose 68 was synthesized from cu-but-2-ene-l,4-diol 66 via the Sharpless asymmetic epoxidation product 67, and was converted into 6-azido-6-deoxy-L-galocro-heptulose 69 by an enzyme-catalyzed aldol condensation (Scheme 13). 3-Azido-3-deoxy-L-etythrose, and thence 6-azido-6-deoxy-L-g/uco-heptulose were obtained in a similar way via 4-rerf-butyldiphenylsilyoxy-rraiu-but-2-enal. These and two other azido-heptulose isomers made from the enantiomeric 3-azido-3-deoxy-tetroses, were converted to a- and P-l-homonojirimycin and homomannonojirimycin on hydrogenation. Ethyl 3-azido-2,3-dideoxy-D-eryr/iro-pentopyranoside and its 3-C-methyl analogue 71, R=H or Me, were synthesized from crotonaldehyde or 3-methyl-2-... 

Azido-2-deoxy- and 2,4-diazido-2,4-dideoxy-D-glucose have been synthesized from derivatives of l,6 2,3-dianhydro-j8-D-mannopyranose as indicated in Scheme 57 339 Other azido-sugars and a 5 -azido-5 -deoxynucleoside are mentioned in Chapters 8 and 21, respectively. 

---