Structure and synthesis in the group of deoxy‐sugars

Abstract

an anhydro-sugar derivative of the ethylene oxide type with a hydrogen halide (e.g. HBr or HCl) resulted in the formation of halogeno-sugar derivatives. For example, when 4 : 6-benzylidene-z : 3-anhydro-a-methylalloside (IV) was treated with hydrogen bromide it gave 3-bromo-3-deoxy-amethylglucoside (V) and 2-bromo-z-deoxy-a-methylaltroside (VI). C,atalytic hydrogenation of these produced 3-de0xy-amethylglucoside (VI 1) and 2-deoxy-a-methyl altroside (VII I) this provided a method of synthesis Of deoxy-sugars. This method has been used also by Reichstein and his coueagues.'O Several methods of synthesis of 2-deoxyribose are outlined and crystalline derivatives of the sugar suitable for its characterization are described. The reactions of this sugar have been studied and methylglrcopyranoddes and the ag-furanoside it have been prepared. The constitutions of these glycosides have been established by various methods. That the reactions of n-deoxyribose are general for other 2-deoxy-sugars was demonstrated by carrying out similar conversions with z-deoxyglucose and z-deoxpgalactose. CH70H CH,OHIt has been shown that the methylene (deoxy) group at position C , of the sugar greatly increases the lability of substituents on the glycosidic carbon atom. Preliminary investigations with suitable derivatives of 2 : 3-dideoxyglucose indicate t h a t the introduction of another deoxy group adjacent to that at C, in the sugar enhances this eifect.H OH CH,OH 80 Green,