Primary Alcohol Groups in Carbohydrates to Carboxylic Acids

1 Primary Alcohol Groups in Carbohydrates to Carboxylic Acids 

A typical list of secondary carbohydrate oxidations is given in Table 2.3 bnt we start with primary alcohol oxidations in furanoses. Work on nncleosides and nncleotides is included in this section. 

Oxidation of the 5 -hydroxy group of 2, 3 -0-isopropylideneadenosine to the corresponding 5 -carboxylic acid was effected by RuCyaq. Na(10 )/CCl -CH3CN (Fig. 2.10) [334]. 

Purine and pyrimidine nucleosides of AZT (Zidovudine, 3 -azido-3 -deoxythymidine) with [RuO ] (from RuClj/K S O/aq. M KOH) gave l-((3-azido-2,3-dideoxy-P-D-eryf/tro-pentafuranosyl-5-uronic acid)-thymine (Fig. 2.11) [335]. 

Primary alcohol groups in several protected ribo-, fructo- and glucofuranoses including 2,3,4-tri-O-benzoyl-D-glucose, 1,2-isopropylidene-D-xylo-furanose, 2,3 4,5-di-0-isopropylid-ene-D-fructopyranose, methyl 2,3-O-isopropylidene-P-D-ribofuranoside, l,2-0-isopropylidene-3,5-0-benzylidene-D-glucofuranose and 

---