167076-54-2Relevant articles and documents
Synthesis of enantiomerically pure (R)-and (S)-1-benzoyloxypropane-2,3-diol and revision of the stereochemical outcome of the Candida antarctica lipase-catalyzed benzoylation of glycerol
Casati, Silvana,Ciuffreda, Pierangela,Santaniello, Enzo
experimental part, p. 658 - 661 (2011/07/08)
Enantiomerically pure (R)- and (S)-1-benzoyloxypropane-2,3-diol have been prepared from (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol and used as reference compounds to correct the reported stereochemical outcome of the Candida antarctica lipase (CAL)-cat
NUCLEOPHILIC DISPLACEMENT REACTIONS OF THE METHANESULFONATES OF THE 1-O-BENZOYL-1,2-, -1,3-, AND -1,4-GLYCOLS
Takano, Seiichi,Hirama, Michiyasu,Seya, Kazuhiko,Ogasawara, Kunio
, p. 4233 - 4236 (2007/10/02)
Nucleophilic displacement reactions of the methanesulfonates (8a-c) of the 1-O-benzoyl-1,2-, -1,3-, and -1,4-glycols (7a-c) with potassium acetate in boiling acetic anhydride have been examined.Both benzoyloxy-group participation pathway (path A) and SN2 displacement pathway (path B) have been involved in the 1,2-(8a)- and 1,3-(8b)-substrates to give a mixture of the primary (10a,b) and the secondary (11a,b) acetates with complete inversion of chiralities.On the other hand, only SN2 displacement pathway (path B) has been involved in the 1,4-substrate (8c) to give the secondary acetate (11c) with inversion of the chirality.
