1207973-87-2

Upstream product

• 186581-53-3 diazomethane 
• 3160-59-6 N-benzyloxycarbonylamino-D-alloisoleucine 

Downstream Products

• 1207973-74-7 C₁₅H₂₁NO₄ 
• 1616868-64-4 (3R,4S)-3-benzyloxycarbonylamino-4-methylhexane-1-sulfonic acid 
• 872423-93-3 (3R,4S)-4-methyl-3-({[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid 
• 1616868-46-2 (3R,4S)-3-(benzyloxycarbonylamino)-4-methylhexyl methanesulfonate 
• 1616868-56-4 (3R,4S)-S-3-(benzyloxycarbonylamino)-4-methylhexyl ethanethioate 

Relevant academic research and scientific papers

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

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.