33156-28-4

Basic information

• Product Name: Ramnodigin
• Synonyms: Ramnodigin;14-Hydroxy-3beta-((2,3,6-trihydroxy-alpha-L-erythro-hexopyranosyl)oxy)-5beta-card-20(22)-enolide;Ramnodigin [inn];Ramnodiginum;Unii-Z8sry7br30
• CAS NO: 33156-28-4
• Molecular Formula: C29H44O6
• Molecular Weight: 488.661
• Mol File: 33156-28-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 646.6°Cat760mmHg
• Flash Point: 209.4°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 1.89E-19mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: Ramnodigin(CAS DataBase Reference)
• NIST Chemistry Reference: Ramnodigin(33156-28-4)
• EPA Substance Registry System: Ramnodigin(33156-28-4)

Safety Data

• Hazardous Substances Data: 33156-28-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C29H44O6/c1-17-24(30)6-7-26(34-17)35-20-8-11-27(2)19(15-20)4-5-23-22(27)9-12-28(3)21(10-13-29(23,28)32)18-14-25(31)33-16-18/h14,17,19-24,26,30,32H,4-13,15-16H2,1-3H3/t17-,19+,20-,21+,22-,23+,24+,26+,27-,28+,29?/m0/s1

Upstream product

• 33156-27-3 Acetic acid (2S,3R,6R)-6-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydro-furan-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester 
• 29742-88-9 (Digitoxigenin-3-yl)-4-O-acetyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid 
• 865484-73-7 tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 1256497-84-3 C₂₉H₄₀O₆ 
• 33156-32-0 C₂₉H₄₂O₆ 
• 247244-65-1 L-aculose 
• 4208-64-4 (S)-1-(2-furanyl)ethanol 
• 143-62-4 (+)-digitoxigenin 

Relevant articles and documents

Synthesis and evaluation of the α- D -/α-l-rhamnosyl and amicetosyl digitoxigenin oligomers as antitumor agents

A highly regio- and stereoselective asymmetric synthesis of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation followed by bis-/tris-dihydroxylation or bis-/tris-diimide reduction. The α-l-rhamnose and α-l-amicetose digitoxin monosaccharide analogues displayed stronger apoptosis inducing activity and cytotoxicity against nonsmall cell human lung cancer cells (NCI-H460) than its d-diastereomeric isomers in a sugar-chain length dependent manner.

C5′-alkyl substitution effects on digitoxigenin α-l-glycoside cancer cytotoxicity

A highly regio- and stereoselective asymmetric synthesis of various C5′-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5′-methyl group in both α-l-rhamnose and α-l-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5′-stereocenter.