1453087-21-2Relevant academic research and scientific papers
One-Pot 2-o-alkylation of l -ascorbic acid
Thopate, Shankarr.,Dengale, Rohita.,Kulkarni, Mukundg.
, p. 1555 - 1557 (2013)
One-pot 2-O-alkylation of l-ascorbic acid involving an in situ 3-O-silylation and desilylation sequence was investigated. Initially the 3-OH group was masked with a t-butyldimethylsilyl (TBDMS) group followed by alkylation of the 2-OH group. Removal of the TBDMS group using 20% sulfuric acid also resulted in hydrolysis of the 5,6-O-isopropylidene to give 2-O-alkyl derivatives of l-ascorbic acid. Selective removal of the 3-O-TBDMS with tetrabutylammonium fluoride (TBAF) gave 5,6-O-isopropylidene-2-O-alkyl derivatives of l-ascorbic acid in good overall yields. Through the application of this protocol, 5,6-O-isopropylidene 2-O-alkyl derivatives of l-ascorbic acid as well as 2-O-alkyl derivatives of l-ascorbic acid may be easily accessed. Georg Thieme Verlag Stuttgart · New York.
