88337-87-5Relevant academic research and scientific papers
Synthesis of a xylosylated rhamnose pentasaccharide - The repeating unit of the O-specific side chain of lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18
Zhang, Jianjun,Kong, Fanzuo
, p. 89 - 97 (2007/10/03)
A xylosylated rhamnose pentasaccharide, α-L-Rhap-(1→3)-[β-L-Xylp-(1→ 2)-] [β-L-Xylp-(1→4)-]α-L-Rhap-(1→3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1→3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-α-L- rhamnopyranosyl-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).
Phenylselenoglycosides as novel, versatile glycosyl donors. Selective activation over thioglycosides
Mehta,Pinto
, p. 4435 - 4438 (2007/10/02)
Selective activation of phenylselenoglycosides over ethylthioglycosides with silver trifluoromethanesulfonate and anhydrous potassium gives an efficient synthesis of disaccharides from selenoglycoside donors and thioglycoside acceptors. Activation is quenched by addition of 1,1,3,3-tetramethylurea or collidine.
The in Situ Activation of Thioglycosides with Bromine: An Improved Glycosylation Method
Kihlberg, Jan O.,Leigh, David A.,Bundle, David R.
, p. 2860 - 2863 (2007/10/02)
A one-step conversion of thioglycosides into 1,2-trans- or 1,2-cis-O-glycosides was accomplished, in situ, by treatment with bromine in the presence of a glycosyl acceptor and a promoter such as silver triflate or mercuric cyanide.This mild "one-pot" proc
ARTIFICIAL CARBOHYDRATE ANTIGENS: A BLOCK SYNTHESIS OF A LINEAR, TETRASACCHARIDE REPEATING-UNIT OF THE Shigella flexneri VARIANT Y POLYSACCHARIDE
Wessel, Hans-Peter,Bundle, David R.
, p. 301 - 312 (2007/10/02)
Glycosylation of methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside with 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide gave methyl 2,4-di-O-benzoyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (4) in 93percent yield.Conversion of 4 into th
