850004-34-1

Upstream product

• 850004-33-0 O-triisopropylsilyl-O-[2,4-di-O-benzyl-3-hydroxy-β-D-xylopyranosyl-(1->4)]-O-2,3-O-isopropylidene-β-L-rhamnopyranoside 
• 156058-53-6 1,2,3-tri-O-acetyl-(3-C-benzyloxymethyl)-β-D-erythrofuranose 
• 182212-10-8 1-O-allyl-D-xylopyranoside 
• 13154-24-0 triisopropylsilyl chloride 
• 87-72-9 D-Xylose 
• 850004-55-6 (3R,4S,5R)-2-Allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-ol 
• 850004-54-5 triisopropyl 4-O-acetyl-2,3-di-O-isopropylidene-L-rhamnopyranose 
• 850004-31-8 triisopropyl 2,3-di-O-isopropylidene-β-L-rhamnopyranose 

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 potent immunostimulatory adjuvant QS-21A

QS-21A 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 clinical trials involving QS-21A as a critical component for immune response augmentation in microgram doses. Herein is reported the first synthesis and structure verification of QS-21Aapi, applying novel glycosylation methodologies in the convergent modular construction of this rare and potent natural product immunostimulant. Copyright