176776-17-3

Upstream product

• 73-34-7 6-deoxy-L-galactose 
• 100-51-6 benzyl alcohol 

Downstream Products

• 176776-18-4 benzyl 3,4-O-isopropylidene-L-fucopyranoside 
• 176666-63-0 Dithiocarbonic acid O-((3aR,4S,7S,7aR)-6-benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester S-methyl ester 
• 50611-09-1 benzyl 2-O-acetyl-3,4-di-O-mesyl-β-L-fucopyranoside 
• 50611-08-0 Acetic acid (2S,3S,4R,5S,6S)-2-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis

Highly (Z)-diastereoselective approaches for the synthesis of trifluoromethylated exo-glycals by copper and photoredox catalysis are described. These complementary reactions are applicable to a wide range of methylene exo-glycals generated from the corresponding pyranoses and furanoses and give trifluoromethylated compounds under mild conditions in moderate to good yields. DFT calculations have allowed a rationalization of the observed (Z)-stereoselectivity.

Synthesis and Biological Evaluation of O-Methylated Glycolipids Related to PGLs via Direct Stereoselective Glycosidation and Sequential Suzuki–Miyaura Coupling using Boracyclane

Synthesis of O-methylated glycolipids via direct stereoselective glycosidation whose sugar moieties are related to those in phenolic glycolipids (PGLs) is reported. Treatment of 2-O-methyl-rhamnosyl imidates with I2 and nBu4NOTf resulted in their activation under low temperature and provided the α-rhamnosides with excellent α-selectivity. nBu4NOTf enhanced the electorophilicity of iodine. This methodology improved the efficiency of the synthesis of both PGL-1 and PGL-tb1 sugars. The process involved the formation of 2-O-naphthylmethyl-α-rhamnoside and 2-O-methyl-α-fucoside. Sequential Suzuki–Miyaura coupling using synthetic glycosides, boracyclane, and aryl bromides provided glycolipids related to PGL sugars, and was accomplished with a one-pot process. Finally, we elucidated the immunosuppressive activities of all these synthetic compounds and found that a phenyl 3-O-α-rhamnosyl-2-O-methyl-α-rhamnoside possessing a 6-(2-naphthyl)hexyl group exhibited the strongest inhibitory effect.

Bengazoles C-G from the sponge Jaspis sp. Synthesis of the side chain and determination of absolute configuration

Five new antifungal bengazoles (C-G) were isolated and fully characterized from a marine sponge of the genus Jaspis sp. Bengazoles C-G, together with the known bengazoles A and B, comprise a homologous series of n, iso, and anteiso fatty acid esters (C13-C16) of the same heterocyclic bis(oxazolyl)methanol parent. The complete relative and absolute configurations of the bengazoles were determined by application of the modified Mosher method and interpretation of exciton coupling in the CD spectra of the tetra-p-bromobenzoate derivatives of bengazole A and that of a model tetrol synthesized in seven steps from L-fucose.