951767-71-8

Upstream product

• 100-39-0 benzyl bromide 
• 303752-86-5 (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol 
• 100759-11-3 allyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-α-D-galactopyranoside 
• 1177264-18-4 C₃₄H₃₄O₅S 
• 87470-72-2 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 202812-10-0 (2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 303752-87-6 O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate 
• 160280-67-1 (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol 
• 160280-66-0 (2S,3S,4R)-2-azido-1-(trityloxy)octadecane-3,4-diol 
• 117168-59-9 (2S,3S,4R)-2-azido-1,3,4-octadecanetriol 
• 554-62-1 D-ribo-phytosphingosine 
• 1201598-10-8 O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate 

Downstream Products

• 1201598-11-9 C₅₉H₇₇N₃O₈ 
• 1309198-89-7 C₆₆H₈₁N₃O₉ 
• 1309198-90-0 C₆₇H₈₅N₃O₈ 
• 1309198-93-3 C₆₈H₈₇N₃O₈ 
• 1352408-17-3 3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-6-hydroxy-6-iodo-α-D-galactopyranosyl)-2-(6-phenylhexanoyl)aminooctadecane-1,3,4-triol 
• 1352408-19-5 3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-2-(6-phenylhexanoyl)aminooctadecane-1,3,4-triol 
• 1352408-20-8 3,4-dihydroxy-1-O-(3,4,5-trihydroxy-α-D-galactopyranosyl)-2-(6-phenylhexanoyl)aminooctadecane-1,3,4-triol 
• 1352408-21-9 C₃₆H₆₁NO₁₀ 
• 1352408-14-0 2-azido-3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)octadecane-1,3,4-triol 
• 1352408-15-1 3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-2-(6-phenylhexanoyl)aminooctadecane-1,3,4-triol 

Relevant academic research and scientific papers

Synthesis and Th1-immunostimulatory activity of α-galactosylceramide analogues bearing a halogen-containing or selenium-containing acyl chain

A novel series of CD1d ligand α-galactosylceramides (α-GalCers) were synthesized by incorporation of the heavy atoms Br and Se in the acyl chain backbone of α-galactosyl-N-cerotoylphytosphingosine. The synthetic analogues are potent CD1d ligands and stimulate mouse invariant natural killer T (iNKT) cells to selectively enhance Th1 cytokine production. These synthetic analogues would be efficient X-ray crystallographic probes to disclose precise atomic positions of alkyl carbons and lipid–protein interactions in KRN7000/CD1d complexes.

Potent Neutralizing Antibodies Elicited by RBD-Fc-Based COVID-19 Vaccine Candidate Adjuvanted by the Th2-Skewing iNKT Cell Agonist

The development of a safe and effective COVID-19 vaccine is of paramount importance to terminate the current pandemic. An adjuvant is crucial for improving the efficacy of the subunit COVID19 vaccine. α-Galactosylceramide (αGC) is a classical iNKT cell agonist which causes the rapid production of Th1- and Th2-associated cytokines; we, therefore, expect that the Th1- or Th2-skewing analogues of αGC can better enhance the immunogenicity of the receptor-binding domain in the spike protein of SARS-CoV-2 fused with the Fc region of human IgG (RBD-Fc). Herein, we developed a universal synthetic route to the Th1-biasing (α-C-GC) and Th2-biasing (OCH and C20:2) analogues. Immunization of mice demonstrated that αGC-adjuvanted RBD-Fc elicited a more potent humoral response than that observed with Alum and enabled the sparing of antigens. Remarkably, at a low dose of the RBD-Fc protein (2 μg), the Th2-biasing agonist C20:2 induced a significantly higher titer of the neutralizing antibody than that of Alum.

A comparison of benzyl and 2-naphthylmethyl ethers as permanent hydroxyl protecting groups in the synthesis of α-galactoglycosphingolipids KRN7000 and PBS-57

Due to the interest in the biological properties of marine derived α-galactoglycosphingolipids (α-GalGSLs), a lot of work has focused on the development of their synthesis. Here we conducted the direct comparison of benzyl and 2-naphthylmethyl (Nap) ether

Divergent synthetic approach to 6′′-modified α-GalCer analogues

A synthetic approach is presented for the synthesis of galacturonic acid and d-fucosyl modified KRN7000. The approach allows for late-stage functionalisation of both the sugar 6′′-OH and the sphingosine amino groups, which enables convenient synthesis of promising 6′′- modified KRN7000 analogues. The Royal Society of Chemistry 2011.

Introduction of aromatic group on 4′-OH of α-GalCer manipulated NKT cell cytokine production

The glycosphingolipid α-GalCer has been found to influence mammalian immune system significantly through the natural killer T cells. Unfortunately, the pre-clinical and clinical studies revealed several critical disadvantages that prevented the therapeutic application of α-GalCer in treating cancer and other diseases. Recently, the detailed illustration of the CD1d/α-GalCer/NKT TCR complex crystal structural, together with other latest structural and biological understanding on glycolipid ligands and NKT cells, provided a new platform for developing novel glycolipid ligands with optimized therapeutic effects. Here, we designed a series of novel aromatic group substituted α-GalCer analogues. The biological activity of these analogues was characterized and the results showed the unique substitution group manipulated the immune responses of NKT cells. Computer modeling and simulation study indicated the analogues had unique binding mode when forming CD1d/glycolipid/NKT TCR complex, comparing to original α-GalCer.