103383-31-9

Basic information

• Product Name: 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose
• Synonyms: 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose
• CAS NO: 103383-31-9
• Molecular Weight: 601.613
• Mol File: 103383-31-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose(103383-31-9)
• EPA Substance Registry System: 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose(103383-31-9)

Safety Data

• Hazardous Substances Data: 103383-31-9(Hazardous Substances Data)

Upstream product

• 2578-45-2 2-chloro-3,5-dinitropyridine 
• 86795-38-2 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside 
• 59055-57-1 methyl 2,3,4-tri-O-benzyl-α-L-rhamnopyranoside 
• 100-44-7 benzyl chloride 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 

Downstream Products

• 103368-07-6 (3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 
• 103368-07-6 (3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 
• 508-93-0 digitoxigenin 3-(α-L-rhamnopyranoside) 

Relevant articles and documents

Cardiac Glycosides. 7. Sugar Stereochemistry and Cardiac Glycoside Activity

Digitoxigenin α-L, β-L, α-D, and β-D-glucosides; α-L-, β-L-, α-D-, and β-D-mannosides; and α-L- and β-L-rhamnosides were stereoselectively synthetized from the corresponding sugar tetrabenzyl trichloroacetimidates.The Na+, K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those digitoxigenin, digitoxigenin 6'-hydroxy-β-D-digitoxide, digitoxigenin β-D-galactoside, and digitoxigenin β-D-digitoxoside.The observed activities reveal that a given sugar substituent may have a role in bindingof some glycoside stereoisomers, but not others.With α-L- and possibly β-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the N+, K+-ATPase receptor.Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the α-L isomer.However, with the β-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains.With β-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly.With these β-D-glycosides, and equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.