Synthesis of 4-O-α-D-Mannopyranosyl-L-rhamnopyranose
TLDR
In this paper, a disaccharide was synthesized in 55% yield by condensation of 2,3,4,6-tetra-O-benzoyl- α-D-mannopyranosyl bromide with methyl 2.3,O-isopropylidene-α-L-rhamno-pyranoside using mercuric cyanide in acetonitrile.Abstract:
4-O-α-D-Mannopyranosyl- L-rhamnopyranose has been synthesized in 55% yield by condensation of 2,3,4,6-tetra-O-benzoyl- α-D-mannopyranosyl bromide with methyl 2,3-O-isopropylidene-α-L-rhamno-pyranoside using mercuric cyanide in acetonitrile (Helferich reaction). The disaccharide has m.p. 143–145°, [α]D + 53.0° → 60.3° (c, 1.0 water), and was characterized as the crystalline peracetates of the disaccharide (m.p. 149.5–150.5°, [α]D − 4.4° (c, 4.3 chloroform)) and of the derived alditol (m.p. 84−85°, [α]D −4.4° (c, 1.9 chloroform)).read more
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Book ChapterDOI
Applications of Gas-Liquid Chromatography to Carbohydrates :Part I°
TL;DR: In this paper, the authors discuss the application of trimethylsilyl derivatives of carbohydrates in gas-liquid chromatography and the use of this method in the analysis of plant materials.
Journal ArticleDOI
Synthèse et étude R.M.N. de disaccharides et trisaccharides dans la série du l-rhamnose
Colette Laffite,Anne-Marie Nguyen Phuoc Du,Francois Winternitz,Renée Wylde,Flore Pratviel-Sosa +4 more
TL;DR: In this paper, the anomeric configuration of l -rhamnose saccharides was determined from the chemical shifts of H-5 and CH3, and a shielding of the methyl group and a deshielding of the H5 proton were observed.
Journal ArticleDOI
Glycosylation of 1,2-O-cyanoethylidene derivatives of carbohydrates
Vitali I. Betaneli,Leon V. Backinowsky,Narguiz É. Byramova,Michael V. Ovchinnikov,Miroslav M. Litvak,Nikolay K. Kochetkov +5 more
Journal ArticleDOI
Synthesis of 4-O-β-D-mannopyranosyl-L-rhamnopyranose
TL;DR: In this paper, the title disaccharide was synthesized in 50% overall yield by way of condensation of 4,6-di-O -acetyl-2,3- O -carbonyl-α- D -mannopyranosyl bromide 5 with methyl 2,3, O -isopropylidene-α, L -rhamnopyranose (1 ) in chloroform solution, in the presence of silver oxide.
Journal ArticleDOI
Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters
Leon V. Backinowsky,Yury E. Tsvetkov,Nikolay F. Balan,Narguiz É. Byramova,Nikolay K. Kochetkov +4 more
TL;DR: The reaction of sugar 1,2-thio-orthoesters in the d-gluco, d- galacto, d - manno, and l - rhamno series with primary and secondary trityl ethers of monosaccharides, in the presence of triphenylmethylium perchlorate as catalyst, affords, stereospecifically, derivatives of 1 2 trans-disaccharide in good yields.
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