2-azido-2-deoxy-D-galactose

A search for an improved synthesis of a-D-galactosaminides has prompted studies on the synthesis of 2-azido-2-deoxy-D-galactose derivatives, such as (8), by addition of the pseudohalogens N3CI, NaBr, and N3ONO2 to tri-O-acetyl-D-galactal. In all cases the galacto- somcr predominated. ... 

The tunicamine derivative 33 has been synthesized from 2-azido-2-deoxy-D-galactose. L-Sorbose has been used as a substrate for symthesizing 1-deoxynojirimycin via the azide 34, which was converted to the antibiotic in a one-pot reaction. Another synthesis employs methyl... 

The synthesis of tunicamycin V using a 2-azido-2-deoxy-D-galactose derivative as starting material for a multistep sequence has been described. ... 

M. Kiso, A. Yasui, and A. Hasegawa, Synthesis of 2-azido-2-deoxy-3,4 5,6-di-D-isoptopyl-Ueaaualdehydo-D-taaaaosu dimediyl acetal and 4-azido-4K)eoxy-23 5,6.di-0-isoptopyl-idene-uldehydo-D-galactose dimetliyl acetal, Carbohydr. Res. 727 137 (1984). 

The synthesis of oct-2-ulosono-1,4-lactone phenylhydrazones from D-gluconic acid is covered in Chapter 16, while the formation of a 1-C-substituted 1,5-dideoxy-l,5-iminopentitol by reduction of 6-azido-6-deoxy-D-galactose diphenyl-formazan with triphenylphosphine is detailed in Chapter 18. 

Knorr method ), 2-azido-2-deoxy-3-0 -6-D-galactopyranosyl-D-galactose (as a glycoside perester and as a glycosyl bromide... 

The 2-azido 2-deoxy-a-D-altrosyl and -mannosyl-(l- 6)-D-galactose derivatives (51) and (52), respectively, were synthesized from the D-allal derivative (49) initial by an iodo-gfycosidation reaction (Scheme 7). This reaction sequence demonstrated an approach to... 

In the field of 2-aniino-2-deoxY-D-glucose disaccharides the sugar in various derivatised forms has been linked to D-galactose (/9-1,3-link)(and /9-1,6-link),D-glucose (iS-l,3-link), 2-amino-2-deoxy-D-glucose (j8-l,4-link) D-galacturonic acid fi-1,2-link)and L-iduronic acid (a-l,4-link).The 2-amino-2,4-dideoxy-4-fluoro compound (55) has been prepared by the oxazoline method and 2-amino-2-deoxy- -D-mannopyranosyl disaccharides have been produced from oximo-products obtained by use of a 2-deoxy-2-oximo-D-arabino-hexosyl bromide. A 4-amino-4-deoxy-D-rhamnosyl disaccharide (a-l,2-linked) has been made by way of 4-azido-corapounds. 

Representatives of the reverse type of disaccharides - l.e., those with 2-amino-2-deoxy-o-D-galactose in the non-reducing position can be made, for example, by use of the trichloroacetiml-date of 3,4,6-tri- -acetyl-2-azido-2-deoxy-B-D-galactopyranose. 

Azido-3,4,6-tri-0-benzyl-D-galactose 49 was synthesized from tri-O-benzyl-D-galactal 47 by the short, efficient route shown in Scheme 7, the key step being the reaction of the anion formed from the 2-deoxy-lactone 48 with triisopropyl-phenylsulfonyl azide. 2-Azido-3,4,6-tri-0-benzyl-D-mannose was similarly obtained as the sole product from tri-6>-benzyl-D-glucal. In both cases the azide is introduced trans to the substituent at C-4. ... 

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