906652-18-4

Upstream product

• 629-74-3 hexadec-1-yne 
• 450370-39-5 3-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)propanal 
• 906651-98-7 [(S,E)-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadec-4-en-3-yl]-bis carbamic acid tert-butyl ester 
• 906652-15-1 tert-butyl (3S,4S,5R)-4,5-dihydroxy-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadecan-3-ylcarbamate 
• 906652-12-8 {(E)-(S)-1-[2-((2R,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-heptadec-2-enyl}-carbamic acid tert-butyl ester 
• 906652-11-7 (S,E)-1-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)nonadec-4-en-3-amine 
• 906651-94-3 (R,E)-2-methyl-N-(3-((2R,3S,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)propylidene)propane-2-sulfinamide 
• 145411-41-2 hexacosanoyl chloride 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

C-Galactosylceramide diastereomers via Sharpless asymmetric epoxidation chemistry

C-Glycoside analogs of α-galactosylceramide (KRN7000) were synthesized in 19 linear steps with Sharpless asymmetric epoxidation as a key reaction. Opening of a hydroxy epoxide with sodium azide provided an anti vicinal azido diol with inversion of configuration at the azide-bearing carbon while opening with Ti(O-i-Pr)2(N3)2 gave syn vicinal azido diol with retention. The latter, unusual outcome could be rationalized either by invoking Ti-catalyzed intramolecular double SN2 inversion or by epoxide opening/intramolecular delivery of azide from the Ti complex.

Expedient synthesis of the α-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000)

Key reactions in a concise synthesis of an α-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodi