83441-63-8

Upstream product

• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 545-06-2 trichloroacetonitrile 
• 145079-53-4 p-tolyl 2,3,4-tri-O-benzyl-1-thio-D-xylopyranoside 
• 242143-00-6 methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 
• 91-09-8 methyl xyloside 
• 87-72-9 D-Xylose 
• 182212-10-8 1-O-allyl-D-xylopyranoside 

Downstream Products

• 99937-73-2 1-(2,3,4-Tri-O-benzyl-α-D-xylopyranosyl)-2-propanon 
• 99705-78-9 1-(2,3,4-Tri-O-benzyl-β-D-xylopyranosyl)-2-propanon 
• 99701-79-8 Trichlor-N-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)acetamid 
• 99701-77-6 2-(2,3,4-Tri-O-benzyl-β-D-xylopyranosyl)-1-propen 
• 99701-77-6 2-(2,3,4-Tri-O-benzyl-α-D-xylopyranosyl)-1-propen 
• 88287-94-9 N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serine 
• 88287-97-2 N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serylalanylalanine 
• 88287-96-1 N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serylalanylalanine allyl ester 
• 88287-99-4 N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)serylalanylalanylglycylalanine allyl ester 
• 1161421-54-0 C₃₄H₃₆O₅ 
• 1161421-53-9 2-methylphenyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside 
• 1072450-36-2 triisopropylsilyl 2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 1072450-37-3 trichloroacetimidoyl 2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 1117976-94-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzyl-D-xylopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

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.

Automated glycan assembly of xyloglucan oligosaccharides

We report the automated glycan assembly of oligosaccharide fragments related to the hemicellulose xyloglucan (XG). Iterative addition of monosaccharide and disaccharide building blocks to a solid support provided seven cellulose and xyloglucan fragments i

Synthesis of QS-21-xylose: Establishment of the immunopotentiating activity of synthetic QS-21 adjuvant with a melanoma vaccine

(Chemical Equation Presented) A helping hand: The adjuvant QS-21-xylose (see structure; the xylose residue is shown in red) was obtained in pure form by chemical synthesis. When combined with its synthetic apiose isomer to furnish synthetic QS-21 (sQS-21), the saponin combination was shown to aid the production of antibodies in mice when injected with a melanoma vaccine. The preparation of sQS-21 provides access to pure, functional saponin adjuvants of defined composition.

Allyl Esters as Carboxy Protecting Groups in the Synthesis of O-Glycopeptides

The construction of β-D-xylosyl- and α-D-N-acetylgalactosaminylserine and -threonine glycopeptides is carried out by using the allyl ester for selective C-terminal deprotection.The β-glycosidic bond between N-(benzyloxycarbonyl)serine allyl ester and 2,3,

Glycosyl Imidates, 12. - Direct Synthesis of O-α- and O-β-Glycosyl Imidates

1-O-Unsubstituted aldoses afford with halogen-activated nitriles under base catalysis directly O-α- and O-β-glycosyl imidates which can be isolated as stable compounds.Investigations with 2,3,4,6-tetra-O-benzyl- and -acetylglucose (1a, b), trichloroacetonitrile and trifluoroacetonitrile and NaH and K2CO3, respectively, as base have demonstrated, that the β-glucopyranosyl-1-oxido oxygen atom is more nucleophilic (rapid formation of 3a-β, 3b-β, 4a-β, and 4b-β) than the α-glycopyranosyl-1-oxido oxygen atom.Because of the reversibility of these reactions, however,due to the anomeric effect finally the thermodynamically more stable α-imidates 3a-α, 3b-α, 4a-α, and 4b-α are formed exclusively.Therefore O-α- and O-β-glycosyl imidate formation can be conducted highly diastereoselectively. - From trichloroacetonitrile and other 1-O-unsubstituted carbohydrates the imidates 7-α - 13-β were obtained as stable compounds. - Less activated nitriles (chloroacetonitrile, dichloroacetonitrile) have proven not or not so successful in the direct O-glycosyl imidate formation. - N-Aryl ketenimines yielded cleanly base-catalyzed direct O-glycosyl imidate formation.However, because of the irreversibility of this reaction under the reaction conditions only kinetic product formation was observed (leading to the β-imidates 14a-β - 14d-β and 15d-β.Similarly 1-O-unprotected mannose gave only the β-product 16d-β.