81562-22-3

Upstream product

• 98-88-4 benzoyl chloride 
• 124-63-0 methanesulfonyl chloride 
• 13265-84-4 D-glucal 
• 58871-06-0 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol 

Downstream Products

• 1189361-42-9 O-trichloroacetimidoyl {[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-α-D-galactopyranoside 
• 1392506-69-2 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 
• 1189361-01-0 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol 
• 475630-51-4 4-azido-4-deoxy-3,6-di-O-benzoyl-D-galactal 
• 3971-45-7 methyl 2-deoxy-α-D-galactopyranoside 
• 36396-42-6 Methyl-3,4,6-tri-O-benzoyl-2-desoxy-α-D-lyxo-hexopyranosid 
• 36396-43-7 Methyl-3,4,6-tri-O-benzoyl-2-desoxy-β-D-lyxo-hexopyranosid 
• 475630-54-7 C₂₀H₁₉NO₆ 
• 475630-50-3 4-azido-4-deoxy-3,6-di-O-benzoyl-D-galactal 
• 34948-79-3 1,5-anhydro-3,4,6-tri-O-benzoyl-2-deoxy-D-lyxo-hex-1-enitol 
• 81562-23-4 1,4,6-tri-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranose 

Relevant academic research and scientific papers

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.

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.

Synthesis of γ-aminobutyric acid analogs based on carbohydrate scaffolds

γ-Aminobutyric acid analogs based on sugar scaffolds were prepared in six to nine steps starting from d-glucal and d-galactal. The key step in the synthesis is the Vilsmeier-Haack reaction that affords the corresponding 2-C-formyl glycal on treatment with

Glycal-mediated syntheses of enantiomerically pure polyhydroxylated γ- and δ-lactams

Syntheses of new enantiomerically pure γ-lactams 4a,b and δ-lactams 5a,b from D-glucal (3a) and D-galactal (3b) as starting materials are described.

CATION-EXCHANGE RESIN-CATALYZED ADDITION OF METHANOL TO BENZOYLATED 1,5-ANHYDRO-2-DEOXY-D-HEX-1-ENITOLS

1,5-Anhydro-3,4,5-tri-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (1) was boiled under reflux with methanol and AG 50W-X8 cation-exchange resin.A two-product mixture of glycosides (2 and 3) was obtained in 38percent yield, together with 19percent of unreacted material. 1,5-Anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (7) was prepared from 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol by selective benzoylation, from wich the corresponding 4-methansulphonate 8 was obtained.Treatment of 8 with sodium benzoate in hexamethylphosphoric triamide for 72 h at 100 deg C afforded 1,5-anhydro-3,4,6-tri-O-benzoyl-2-deoxy-D-xylo-hex-1-enitol (9) in 52percent yield.An unknow byproduct (B), tentitatively shown to be a tri-O-benzoyl-D-hex-2-enopyranose analog, was also isolated in 14percent yield.The 270-MHz n.m.r. spectrum of B was analyzed in terms of its J1,3, J2,4 and J4,5 coupling constant in relation to the various configurational and conformational possibilities for hex-2-enopyranose, and was identified as 1,4,6-tri-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranose having the oH5 conformation.The analysis presented should also be applicable to pent-2-enopyranose systems.When 9 was treated with methanol in the presence of AG 50W-X8 cation-exchange resin, a mixture of glycosides 4 and 5 was obtained in 47percent yield.The low yields were attributed to methanolysis of the benzoyl groups during the reaction.