40010-55-7Relevant articles and documents
C-1,C-2 Stereospecific Rearrangements of Aldohexoses by Calcium Ion in Basic Solution
Yanagihara, Ryoji,Osanai, Shuichi,Yoshikawa, Sadao
, p. 2273 - 2276 (2007/10/02)
In aqueous or methanolic solution containing Ca(2+) and hydroxide ion, aldoses are rapidly epimerized at C-2.This reaction involves C-1,C-2 stereospecific rearrangement. -D-Mannose is formed from -D-glucose by this reaction.
HYDROXIDE-CATALYZED ISOMERIZATION OF D-(1-13C)MANNOSE: EVIDENCE FOR THE INVOLVEMENT OF 3,4-ENEDIOLS
King-Morris, Melinda J.,Serianni, Anthony S.
, p. 29 - 36 (2007/10/02)
The KOH-catalyzed isomerization of D-(1-13C)mannose under anaerobic conditions was studied by 13C-n.m.r. spectroscopy.D-(1-13C)Glucose and D-(1-13C)fructose are generated during the reaction, as expected.In addition, however, (6-13C)glucose, (6-13C)mannose, and (6-13C)fructose are produced in small proportions, possibly via symmetrical 3,4-enediol intermediates.The involvement of the latter structures in 13C-label shifting is inferred from the observation of (1-13C)sorbose and (6-13C)sorbose in the reaction mixture.