Synthesis of beta-D-ribofuranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 3)-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system

Citation
M. Hirooka et al., Synthesis of beta-D-ribofuranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 3)-L-rhamnopyranose by in situ activating glycosylation using 1-OH sugar derivative and Me3SiBr-CoBr2-Bu4NBr-molecular sieves 4A system, B CHEM S J, 74(9), 2001, pp. 1679-1694
Citations number
134
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
00092673 → ACNP
Volume
74
Issue
9
Year of publication
2001
Pages
1679 - 1694
Database
ISI
SICI code
0009-2673(200109)74:9<1679:SOB-3->2.0.ZU;2-V
Abstract
beta -D-Ribofuranosyl-(1 -->3)-alpha -L-rhamnopyranosyl-(1 -->3)-L-rhamnopy ranose, the trisaccharide repeating unit of the C.freundii O28, 1c O-specif ic polysaccharide, was synthesized using in situ activating glycosylation o f the 1-OH sugar derivatives and a reagent mixture of trimethylsilyl bromid e, cobalt(II) bromide, tetrabutylammonium bromide, and molecular sieves 4A. Regioselective tritylation was useful for synthesizing the 3-OH derivative s of methyl, allyl, and benzyl alpha -L-rhamnosides.