69558-07-2

Upstream product

• 67-56-1 methanol 
• 72657-01-3 1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose 
• 61199-75-5 methyl 4-O-benzyl-2,3-O-(S)-benzylidene-α-L-rhamnopyranoside 
• 61199-76-6 methyl 4-O-benzyl-endo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 100-39-0 benzyl bromide 
• 131337-88-7 methyl 2-O-allyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 100-44-7 benzyl chloride 
• 71715-59-8 methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 73-34-7 L-rhamnose 
• 117249-17-9 3,4-di-O-benzyl-L-rhamnal 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 65529-48-8 methyl endo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 65529-46-6 Methyl exo-2,3-di-O-benzylidene-α-L-rhamnopyranoside 

Downstream Products

• 131337-89-8 methyl 3,4-di-O-benzyl-2-O--α-L-rhamnopyranoside 
• 145243-61-4 3,4-di-O-benzyl-2-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside de methyle 
• 125520-05-0 Methyl 2-O-(3-O-Acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 112107-26-3 methyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 112107-25-2 (2S,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3-ol 
• 71348-34-0 methyl 3,4-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 79681-52-0 methyl 2-O-(4-O-benzoyl-2,3-O-cyclohexylidene-β-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 79681-53-1 methyl 2-O-(4-O-benzoyl-2,3-O-cyclohexylidene-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 115678-25-6 methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 115678-22-3 methyl 2-O-<2-O-(2-O-benzoyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 115678-26-7 methyl 2-O(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 79080-88-9 3,4-di-O-benzyl-6-deoxy-α-L-mannopyranose 
• 148163-95-5 methyl 3,4-di-O-benzyl-2-O-(3,4-di-O-acetyl-2-deoxy-2-iodo-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 71715-59-8 methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Combination of solid phase and solution phase synthesis of oligosaccharides using sonication

An approach that combines solid phase and solution phase synthesis of oligosaccharides via the assistance of sonication has been developed. By employing the traceless linker, the designed oligosaccharides can be obtained in pure form and, more importantly

Methyltrioxorhenium-catalyzed epoxidation-methanolysis of glycals under homogeneous and heterogeneous conditions

The efficient and high yielding domino epoxidation-methanolysis of glycals 8-15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2-acetoxy derivatives 16-23a, b by direct acetylation of the crude mixtures. Homogeneous MTO-amine complexes 5-7, heterogeneous poly(4-vinyl-pyridine)/MTO compounds I-III, and microencapsulated polystyrene/MTO systems IV-VII were also tested and demonstrated their effectiveness as catalysts for the oxidation step. The facial diastereoselectivity of the oxidation ranged from satisfactory to excellent depending on the substrate and could be optimized by ample screening of catalysts. Complete conversions of substrates and nearly quantitative yields of products were obtained under environmentally friendly experimental conditions and with the use of simple work-up procedures.

Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of α- to β-pyranosides and the fragmentation of anomeric radicals

The formation and stereoselective quenching of 1-mannopyranosyl radicals by a tributyltin hydride-mediated intramolecular 1,5-hydrogen abstraction sequence is described. A competing process is 1,4-hydrogen atom abstraction leading principally to glucopyran-2-ulosides. Fragmentation of the anomeric radical resulting in the formation of ring opened products is a problem in certain series. The chemistry is dictated to a considerable extent by the nature of the protecting groups employed with the 4,6-benzylidene series and, for rhamnose, the Ley 3,4-dispiroketal, being particularly susceptible to the 1,4-hydrogen atom abstraction but less to the fragmentation. Photochemical conditions are described, in which these side reactions are practically eliminated, and applied to the inversion of an α- to a β-mannoside in a disaccharide.

Synthesis of disaccharide methyl glycosides related to the polysaccharide from Klebsiella serotype 40 and a study of their inhibition in the precipitin reaction.

The methyl glycosides of alpha-D-Manp-(1----4)-alpha-L-Rhap (3), alpha-L-Rhap-(1----3)-beta-D-Galp (4), beta-L-Rhap-(1----3)-beta-D-Galp (5), beta-D-Galp-(1----2)-alpha-L-Rhap (6), and beta-D-GlcpA-(1----2)-alpha-L-Rhap (7) have been synthesised and their

Synthesis of Some Disaccharides Containing an L-Rhamnopyranosyl or L-Mannopyranosyl Residue, and the Substrate-specificity of α-L-Rhamnosidase from Aspergillus niger

In order to investigate the substrate-specificity of α-L-rhamnosidase from Aspergillus niger, the following disaccharides were synthesized: 2-O-α-L-rhamnopyranosyl-α-D-fucopyranose (1), methyl 4-O-α-L-rhamnopyranosyl-β-L-arabinopyranoside (2), methyl 2-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside (3) and 6-O-α-L-mannopyranosyl-D-glucopyranose (4).The action of α-L-rhamnosidase on compounds 1 - 4 and another fifteen disaccharides containing α- or β-L-rhamnopyranosidic bonds or an α-L-mannopyranosidic bond was examined.As the result, all the disaccharides having an α-L-rhamnopyranosidic linkage were hydrolyzed well, while the ones having β-L-rhamnopyranosidic or α-L-mannopyranosidic linkage could not be hydrolyzed at all.Accordingly, this enzyme might be used for the determination of anomeric configurations of the L-rhamnopyranosidic bond, although further studies on the specificity of the enzyme are required.

A NOVEL REDUCTIVE RING-OPENING OF CARBOHYDRATE BENZYLIDENE ACETALS

Further examples are given of a facile, highly regioselective, reductive opening of benzylidene acetals of hexopyranosides using sodium cyanoborohydride-hydrogen chloride.For dioxolane benzylidene acetals, the direction of reductive opening of the five-me

Direct and Efficient Synthesis of β-L-Rhamnopyranosides

Methyl α-L-rhamnopyranoside (1) was converted in a single-stage procedure to crystalline methyl 4-O-benzoyl-2,3-O-cyclohexylidene-α-L-rhamnopyranoside (2).This compound served as a stable derivative from which 4-O-benzoyl-2,3-O-cyclohexylidene-α-L-rhamnop