351900-97-5

Upstream product

• 73445-31-5 benzoyl 3,4,6-tri-O-benzyl-2-O-benzoyl-β-D-galactopyranoside 
• 57690-62-7 methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 351900-88-4 methyl 1,2-anhydro-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-α-D-glucuronate 
• 351900-96-4 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 
• 351900-87-3 methyl 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-glucuronate-D-glycal 
• 351900-86-2 methyl 3-O-(tert-butyldimethylsilyl)-glucuronate-D-glycal 
• 95530-80-6 methyl 1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 148926-02-7 2-O-benzoyl-3,4,6-tri-O-benzyl-D-galactopyranose 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 

Downstream Products

• 850004-60-3 O-4-methoxybenzyl-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->3)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 351900-98-6 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzoyl-β-D-xylosyl)-(1->3)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 850004-42-1 O-trichloroacetimidoyl-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->3)]-6-O-methyl-4-O-acetyl-α-D-glucuronate 

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.

Synthesis of the trisaccharide portion of the immunologic adjuvant QS-21A via sulfonium-mediated oxidative and dehydrative glycosylation.

[see structure]. The first synthesis of the trisaccharide fragment of the potent immunologic adjuvant QS-21A is reported. The key steps involve the application of sulfonium-mediated oxidative and dehydrative glycosidic couplings to construct the anomeric