86651-74-3

Upstream product

• 206269-18-3 1-O-acetyl-2,3,6-trideoxy-α,β-DL-glycero-hex-2-enopyranos-4-ulose 
• 86670-21-5 benzyl 3-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 33647-89-1 2-methyl-6-acetoxy-3-oxo-3,6-dihydro-2H-pyran 

Downstream Products

• 89734-12-3 benzyl 2-O-(4-O-acetyl-α-L-rhamnopyranosyl)-3-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 89734-10-1 benzyl 2-O-(4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-3-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 89734-11-2 Benzoic acid (2R,3R,4R,5S,6S)-2,5-bis-benzyloxy-3-((2S,5R,6S)-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

A new method of oligosaccharide synthesis: rhamnobioses

A semi-synthetic approach to (1->2)-α- and (1->3)-α-linked rhamnobioses is presented.The method involves condensation of benzyl 2-O- or 3-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (5) with 1-O-acetyl-2,3,6-trideoxy-α,β-DL-glycero-hex-2-enopyranos-4-ulose(6), isolation of the L-L and D-L forms of the resulting disaccharide derivatives, reduction of the carbonyl groups to give α-erythro unsaturated products, and cis-hydroxylation to form the rhamnobiose derivatives.Removal of the protecting groups then gave α-L-Rhap-(1->2)-L-Rhap, α-L-Rhap-(1->3)-L-Rhap, and the corresponding D-L stereoisomers.The (1)H- and (13)C-n.m.r. data are of diagnostic value in differentiating the stereoisomers. 1-(2-Furyl)ethanol was resolved into its enantiomers, and the (+)-form was converted into (+)-6 which in turn was condensed with 5.The structure of the products indicated that (+)-1-(2-furyl)ethanol has the R configuration.

CRYSTAL AND MOLECULAR STRUCTURES OF BENZYL 3-O-BENZOYL-4-O-BENZYL-2-O-(2,3,6-TRIDEOXY-α-L-GLYCERO-HEX-2-ENOPYRANOSYL-4-ULOSE)-α-L-RHAMNOPYRANOSIDE

Benzyl 3-O-benzoyl-4-O-benzyl-2-O-(2,3,6-trideoxy-α-L-glycero-hex-2-enopyranosyl-4-ulose)-α-L-rhamnopyranoside has been investigated by X-ray diffraction methods.The crystals obtained from aqueous ethanol are orthorombic, space group P212121 with cell konstans a = 10.775(2), b = 10.857(2), and c = 25.774(3) Angstroem.A four-circle, automatic diffractometer was used for intensity data collection.Out of 3370 reflection intensities, 2634 were of I > 2?I and these were used for refinement.The structure was solved by direct methods, and the atomic parameters were then refined by the full-matrix, least-squares procedure.The unsaturated dihydropropanone ring adopts a deformed sofa conformation, whereas the rhamnopyranose ring adopts a chair conformation.The glycosidic linkage is characterised by torsion angles Φ33(2) deg and Ψ-13(1) deg.A new classification for the conformations of glycosidic linkages is suggested.