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Structure and synthesis in the group of deoxy‐sugars
Author(s) -
Overend W. G.,
Stacey M.
Publication year - 1950
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.2740010603
Subject(s) - lability , sugar , chemistry , deoxyribose , glycosidic bond , methylene , group (periodic table) , glycoside , amino sugar , carbohydrate , carbon atom , stereochemistry , monosaccharide , organic chemistry , biochemistry , ring (chemistry) , dna , enzyme
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 methylglycopyranosides and the αβ‐furanoside of it have been prepared. The constitutions of these glycosides have been established by various methods. That the reactions of 2‐deoxyribose are general for other 2‐deoxy‐sugars was demonstrated by carrying out similar conversions with 2‐deoxyglucose and 2‐deoxygalactose. It has been shown that the methylene (deoxy) group at position C 2 of the sugar greatly increases the lability of substituents on the glycosidic carbon atom. Preliminary investigations with suitable derivatives of 2 : 3‐dideoxyglucose indicate that the introduction of another deoxy group adjacent to that at C 2 in the sugar enhances this effect.