73395-15-0Relevant academic research and scientific papers
Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences
Pastore, Antonello,Adinolfi, Matteo,Iadonisi, Alfonso,Valerio, Silvia
scheme or table, p. 1316 - 1323 (2010/10/02)
Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f
Efficient synthesis of man2, man3, and man 5 oligosaccharides, using mannosyl iodide donors
Lam, Son N.,Gervay-Hague, Jacquelyn
, p. 8772 - 8779 (2007/10/03)
A highly efficient protocol for making Man3 and Man5 oligosaccharides with use of orthogonally protected glycosyl iodide donors has been developed. Glycosylation of a C-2-O-acetyl mannosyl iodide donor in the presence of silver trifl
Total synthesis of the Glc3Man N-glycan tetrasaccharide
Ennis,Cumpstey,Fairbanks,Butters,Mackeen,Wormald
, p. 9403 - 9411 (2007/10/03)
The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.
The Selective Monobenzylidenation of Some Monosaccharides and Their Derivatives with α,α-Dimethoxytoluene
Patroni, Joseph J.,Stick, Robert V.,Skelton, Brian W.,White, Allan H.
, p. 91 - 102 (2007/10/02)
The treatment of some monosaccharides and their derivatives with α,α-dimethoxytoluene and an acid catalyst in dimethylformamide at about 80 deg C can lead to selective benzylidenation, e.g. methyl α-D-mannopyranoside gives mainly methyl 4,6-O-benzylidene-α-D-mannoside, together with two other minor monobenzylidene derivatives (2,3-) and two minor dibenzylidene derivatives (2,3:4,6-).The treatment of various other pyranoses and pyranosides is also described.As well, a 1H n.m.r. study of the acid transformation of some of the above α-D-mannosides is reported, together with a single-crystal X-ray diffraction structure determination of a novel monobenzylidene derivative, namely methyl (S)-2,3-O-benzylidene-α-D-mannopyranoside.
CHEMO-, STEREO- AND REGIOSELECTIVE HYDROGENOLYSIS OF CARBOHYDRATE BENZYLIDENE ACETALS. SYNTHESIS OF BENZYL ETHERS OF BENZYL α-D-, METHYL β-D-MANNOPYRANOSIDES AND BENZYL α-D-RHAMNOPYRANOSIDE BY RING CLEAVAGE OF BENZYLIDENE DERIVATIVES WITH THE LiAlH4-AlCl3
Liptak, Andras,Imre, Janos,Harangi, Janos,Nanasi, Pal,Neszmelyi, Andras
, p. 3721 - 3728 (2007/10/02)
Treatment of benzyl α-(1) and methyl β-D-mannopyranoside (2) with α,α-dimethoxytoluene gave the exo and endo isomers (3,5 and 4,6) of the dibenzylidene derivatives of 1 and 2.Hydrogenolysis of the exo isomers (3 and 5) with a molar equivalent of AlH2Cl ga
