1026022-07-0

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 201858-29-9 allyl α-D-isopropylidene-α-D-fucopyranoside 

Downstream Products

• 1026022-08-1 O-allyl 2-O-t-butyldimethylsilyl-3-O-p-methoxybenzyl-α-D-fucopyranoside 
• 1026022-11-6 O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-2-O-t-butyldimethylsilyl-α-D-fucopyranoside 
• 1026022-14-9 O-triisopropylsilyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-Lrhamnopyranose-(1->3)]-β-D-fucopyranoside 
• 1026022-12-7 O-allyl 4-O-acetyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-α-D-fucopyranoside 
• 1026022-09-2 O-allyl 4-O-acetyl-2-O-t-butyldimethylsilyl-3-O-p-methoxybenzyl-α-D-fucopyranoside 

Relevant academic research and scientific papers

TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF

The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

Synthesis and structure verification of the vaccine adjuvant QS-7-Api. Synthetic access to homogeneous Quillaja saponaria immunostimulants

QS-7-Api is an exceedingly potent immuno-adjuvant isolated from the bark of Quillaja saponaria. It is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccine clinical trials. Tedious isolation/purification protocols and uncertainty in its structural constitution have hindered the clinical development of QS-7. A chemical synthesis of QS-7-Api is described, providing structural verification of the adjuvant. A novel semisynthetic sequence to QS-7-Api has also been established, greatly facilitating access to QS-7 for preclinical and clinical evaluation.Copyright