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Beobachtungen zur Synthese der 2‐Deoxy‐ D ‐ribose aus 1, 2; 5, 6‐Diisopropyliden‐3‐mesyl‐ D ‐glucose
Author(s) -
Recondo E.,
Rinderknecht H.
Publication year - 1960
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19600430626
Subject(s) - chemistry , hydrolysis , yield (engineering) , ribose , sodium carbonate , acid hydrolysis , degradation (telecommunications) , stereochemistry , medicinal chemistry , sodium , organic chemistry , enzyme , telecommunications , materials science , computer science , metallurgy
A simplified method for the preparation of 2‐deoxy‐ D ‐ribose from 1, 2; 5, 6‐diisopropylidene‐3‐mesyl‐ D ‐glucofuranose is described. Acid hydrolysis of the latter and alkaline degradation of 3‐mesyl‐ D ‐glucose are effected without isolation of intermediates, the whole operation requiring only 2½ hours. A specific «anion effect » on the velocity of this degradation and on the yield of 2‐deoxy‐ D ‐ribose anilide has been observed. The use of sodium carbonate gives particularly high yields of pure 2‐deoxy‐ D ‐ribose anilide. Improvements in the synthesis of 1, 2; 5, 6‐diisopropylidene‐ D ‐glucofuranose are described.