76850-61-8

Basic information

• Product Name: (2R,3R,4S,5S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol
• CAS NO: 76850-61-8
• Molecular Weight: 288.384
• Mol File: 76850-61-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol(76850-61-8)
• EPA Substance Registry System: (2R,3R,4S,5S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3,4,5-triol(76850-61-8)

Safety Data

• Hazardous Substances Data: 76850-61-8(Hazardous Substances Data)

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 

Downstream Products

• 89734-42-9 (2S,3R,4S,5S,6R)-2-[(2R,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 
• 89734-44-1 (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S)-4,5-Dihydroxy-2-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol 

Relevant articles and documents

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.