1392506-69-2

Basic information

• Product Name: O-triisopropylsilyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside
• Synonyms: O-triisopropylsilyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside
• CAS NO: 1392506-69-2
• Molecular Weight: 1130.46
• Mol File: 1392506-69-2.mol

Chemical Properties

• CAS DataBase Reference: O-triisopropylsilyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: O-triisopropylsilyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside(1392506-69-2)
• EPA Substance Registry System: O-triisopropylsilyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside(1392506-69-2)

Safety Data

• Hazardous Substances Data: 1392506-69-2(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 475630-50-3 4-azido-4-deoxy-3,6-di-O-benzoyl-D-galactal 
• 81562-22-3 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-4-O-mesyl-D-arabino-hex-1-enitol 
• 13265-84-4 D-glucal 
• 242143-00-6 methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 
• 91-09-8 methyl xyloside 
• 87-72-9 D-Xylose 
• 1189361-01-0 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol 
• 1189361-04-3 O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside 
• 1392506-96-5 [2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranose 
• 73-34-7 L-rhamnose 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 182212-10-8 1-O-allyl-D-xylopyranoside 
• 64650-81-3 allyl α-L-rhamnopyranoside 

Relevant articles and documents

TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

TRITERPENE SAPONIN ANALOGUES

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

TRITERPENE SAPONIN ANALOGUES

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

Synthesis and preclinical evaluation of QS-21 variants leading to simplified vaccine adjuvants and mechanistic probes

QS-21 is a potent immunostimulatory saponin that is currently under clinical investigation as an adjuvant in various vaccines to treat infectious diseases, cancers, and cognitive disorders. Herein, we report the design, synthesis, and preclinical evaluation of simplified QS-21 congeners to define key structural features that are critical for adjuvant activity. Truncation of the linear tetrasaccharide domain revealed that a trisaccharide variant is equipotent to QS-21, while the corresponding disaccharide and monosaccharide congeners are more toxic and less potent, respectively. Modification of the acyl chain domain in the trisaccharide series revealed that a terminal carboxylic acid is well-tolerated while a terminal amine results in reduced adjuvant activity. Acylation of the terminal amine can, in some cases, restore adjuvant activity and enables the synthesis of fluorescently labeled QS-21 variants. Cellular studies with these probes revealed that, contrary to conventional wisdom, the most highly adjuvant active of these fluorescently labeled saponins does not simply associate with the plasma membrane, but rather is internalized by dendritic cells.