475630-50-3

Upstream product

• 81562-22-3 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-4-O-mesyl-D-arabino-hex-1-enitol 
• 58871-06-0 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol 
• 98-88-4 benzoyl chloride 
• 13265-84-4 D-glucal 

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 
• 475630-54-7 C₂₀H₁₉NO₆ 
• 475630-52-5 C₂₀H₁₇N₃O₆ 

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 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.

Design and synthesis of potent Quillaja saponin vaccine adjuvants

The success of antitumor and antiviral vaccines often requires the use of an adjuvant, a substance that significantly enhances the immune response to a coadministered antigen. Only a handful of adjuvants have both sufficient potency and acceptable toxicity for clinical investigation. One promising adjuvant is QS-21, a saponin natural product that is the immunopotentiator of choice in many cancer and infectious disease vaccine clinical trials. However, the therapeutic promise of QS-21 adjuvant is curtailed by several factors, including its scarcity, difficulty in purification to homogeneity, dose-limiting toxicity, and chemical instability. Here, we report the design, synthesis, and evaluation of chemically stable synthetic saponins. These novel, amide-modified, non-natural substances exhibit immunopotentiating effects in vivo that rival or exceed that of QS-21 in evaluations with the GD3-KLH melanoma conjugate vaccine. The highly convergent synthetic preparation of these novel saponins establishes new avenues for discovering improved molecular adjuvants for specifically tailored vaccine therapies.

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.