132938-41-1

Upstream product

• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 73-34-7 D-Fucose 
• 612-25-9 2-Nitrobenzyl alcohol 
• 69483-13-2 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 

Downstream Products

• 850004-56-7 2-nitrobenzyl 3-O-benzyl-β-D-fucopyranoside 
• 850004-57-8 (2R,3S,4S,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-ol 
• 850004-58-9 Acetic acid (2R,3S,4S,5R,6R)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yl ester 
• 912805-51-7 acetic acid 4-benzyloxy-5-hydroxy-2-methyl-6-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yl ester 
• 912805-54-0 C₆₄H₈₅NO₂₀Si 
• 133006-28-7 C₇₀H₇₇N₃O₁₃Si 
• 133006-29-8 C₇₀H₇₇N₃O₁₃Si 
• 133006-27-6 C₇₀H₇₇N₃O₁₃Si 
• 132938-57-9 C₇₀H₇₇N₃O₁₃Si 
• 132938-60-4 Ethyl-{(3S,4S,6R)-4-methoxy-6-[(3aS,4R,6R,7R,7aS)-4-methyl-6-(2-nitro-benzyloxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 132938-44-4 Ethyl-{(3S,4S,6S)-4-methoxy-6-[(3aS,4R,6R,7R,7aS)-4-methyl-6-(2-nitro-benzyloxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 132938-48-8 {(3S,4S,6S)-6-[(2R,3R,4S,6R)-5-[(E)-Benzyloxyimino]-6-methyl-2-(2-nitro-benzyloxy)-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl}-ethyl-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 148152-88-9 2,2,2-Trichloro-acetimidic acid (3R,4S,6R)-5-[(E)-benzyloxyimino]-3-{(2S,4S,5S)-5-[ethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-6-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl ester 
• 132938-47-7 {(3S,4S,6S)-6-[(2R,3R,4S,6R)-5-[(Z)-Benzyloxyimino]-4-hydroxy-6-methyl-2-(2-nitro-benzyloxy)-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl}-ethyl-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant academic research and scientific papers

Synthetic studies of complex immunostimulants from Quillaja saponaria: Synthesis of the potent clinical immunoadjuvant QS-21Aapi

QS-21 is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing vaccine therapy clinical trials involving QS-21 as a critical adjuvant component for immune response augmentation. QS-21 is a natural product immunostimulatory adjuvant, eliciting both T-cell- and antibody-mediated immune responses with microgram doses. Herein is reported the synthesis of QS-21 Aapi in a highly modular strategy, applying novel glycosylation methodologies to a convergent construction of the potent saponin immunostimulant. The chemical synthesis of QS-21 offers unique opportunities to probe its mode of biological action through the preparation of otherwise unattainable nonnatural saponin analogues.