66252-76-4Relevant academic research and scientific papers
GLYCOSYLATION OF TRITERPENE ALCOHOLS OF THE LUPANE SERIES
Odinokova, L. E.,Denisenko, M. V.,Denisenko, V. A.,Uvarova, N. I.
, p. 178 - 183 (2007/10/02)
The glycosylation of lupeol, allobetulin, 3β-28-dihydroxy-18-lupene, 3β-28-dihydroxy-18β,19β-epoxylupane and of betulin monoacetates in acetonitrile with mercury cyanide has ben studied.The 3- and 28-mono- and the 3,28-di-O-β-D-glucopyranosides of 3β-28-dihydroxy-18-lupene and of 3β-28-dihydroxy-18β,19β-epoxylupane have been synthesized for the first time.Preparative methods for the synthesis of glucosides of lupeol, of allobetulin, and of betulin 3- and 28-monoacetates are proposed.
GLYCOSYLATION OF BETULIN AND ITS ACETATES IN THE PRESENCE OF CADMIUM CARBONATE
Odinokova, L. E.,Oshitok, G. I.,Denisenko, V. A.,Anufriev, V. F.,Tolkach, A. M.,Uvarova, N. I.
, p. 168 - 173 (2007/10/02)
The glycosylation of betulin and its acetates by α-acetobromoglucose in toluene in the presence of cadmium carbonate is considered.It has been shown that the reaction is accompanied by Wagner-Meerwein rearrangements of the initial alcohols in rings A and E.This leads to the formation - in addition to acetates of betulin glycosides - of derivatives of allobetulin - A-nor-Δ3(5)-allobetulin and A-nor-Δ3(5)-betulin - as was shown by 1H and 13C NMR spectroscopy.
SYNTHESIS OF TRITERPENE AND STEROID GLYCOSIDES
Uvarova, Nina I.,Atopkina, Lyubov N.,Elyakov, Georgi B.
, p. 33 - 42 (2007/10/02)
The glycosylation of cholesterol, β-sitosterol, 28-O-acetylbetulin, and betulin with acylated glycosyl halides in the presence of Hg(OAc)2, Hg(CN)2, CdCO3, Ag2O, Ag2CO3, and HgO + HgBr2 usually gives acylated αβ-glycosides accompanied by acetates, ethers, and bromo and unsaturated derivatives of the initial alcohols.The use of Hg(CN)2 gave mainly β anomers (40-87percent), whereas α anomers preponderated when Hg(OAc)2 was the catalyst.When there was a deficiency of hydrogen halide acceptor and in the presence of the acidic catalyst HgBr2*HBr, the β anomer, produced initially, underwent anomerisation.Cholesteryl α-D-glucopyranoside tetra-acetate (48percent) was obtained by anomerisation of the β anomer.
