76899-39-3

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 

Downstream Products

• 89734-42-9 (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S)-4,5-Dihydroxy-2-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 89734-43-0 (2S,3R,4S,5S)-2-[(2S,3R,4S,5S)-4,5-Dihydroxy-2-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4,5-triol 
• 89734-43-0 (2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-4,5-Dihydroxy-2-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

(13)C-N.M.R. SPECTROSCOPY OF α- AND β-ANOMERIC SERIES OF ALKYL L-ARABINOPYRANOSIDES

Anomeric pairs of L-arabinopyranosides of variety of a aliphatic alcohols, were prepared, and their n.m.r. spectroscopy, especially the glycosylation shift of their (13)C signals, was investigated in comparison with those of D-glucopyranosides, D-mannopyranosides, and L-rhamnopyranosides reported previously.It was found that the glycosylation shift of the L-arabinopyranosides in the present study is almost the same as that of D-glucopyranosides, and the conformational equilibrium of each of these L-arabinopyranosides is very similar to that of the corresponding anomer of methyl L-arabinopyranoside, namely, a preponderance of the 4C1 form, regardless of the structure of the aglycon alcohol.The present results are also useful for structural study of naturally occurring arabinopyranosides.

n.m.r.-spectral stuidies of 2-linked glycosides: 2-O-glycosylation shifts of 2-O-glycosyilated α- and β-L-arabinopyranoides

Anomalous glycosylation shift values of the signals for C-1 (the anomeric carbon atom) and C-2 (the glycosylated carbon atom) were sometimes observed for 2-O-β-D-glycopyranosyl (or -β-D-xylopyranosyl)-β-D-glucopyranosides, whereas no remarkable displacements of the other sugar-carbon signals were observed in these cases.This can be explained in terms of chanmge of the orientation of the glycosyl linkages, owing to strong, steric interaction between the 2-O-glycosyl group and the 1-O-aglycon (or -sugar) group.Various 2-O-glycosylated α- and β-L-arabinopyranosides were synthesized.In the case of α-L-arabinopyranosides, the processes of 2-O-β-D-glucosylation, -β-D-xylosylation, and -α-L-arabinosylation resulted in unexpected, upfield shifts of the C-3, -4, and -5 signals, together with displacement of the C-1 and -2 resonances.Furthermore, significant alteration of the values of 3JH1,H2 and 1JC1,H1 was also observed for the 2-O-glycosylated α-L arabinopyranoside moiety, indicating an increase in the contribution of the 1C4 conformation of the glycosylated α-L-arabinopyranoside in these cases.On the other hand no remarkable variation in the signals of C-3, -4, and -5, or in the 3JH1,H2 and 1JC1,H1 values, was found for 2-O-α-L-rhamnosylation, except for 4-epihederagenin-3-yl 2-O-α-L-rhamnopyranosyl-α-L-arabinopyranoside.In the present study, such unusual 2-O-glycosylation shifts were not encountered for the 2-O-glycosylation of β-L-arabinopyranosides.