144634-18-4

Upstream product

• 352020-76-9 2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranose 
• 906545-82-2 methyl (2R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-methylsulfonyloxy-butanoate 
• 906545-79-7 methyl (2S)-2-hydroxy-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate 
• 906545-78-6 (S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester 
• 906545-84-4 methyl (2S)-2-azido-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate 
• 906545-77-5 (2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 140461-65-0 (2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl alcohol 
• 204187-65-5 (S)-2,2-Dimethyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester 
• 204187-63-3 (S)-2,2-Dimethyl-4-[(Z)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester 
• 140397-46-2 (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal 
• 204187-64-4 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol 

Downstream Products

• 906545-86-6 dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate 
• 906545-87-7 (3S,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-4-oxo-5-nonadecene 
• 906545-88-8 (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-4-hydroxy-5-nonadecene 
• 906545-92-4 (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-4-hydroxy-3-[15(Z)-tetracosenoylamino]-5-nonadecene 
• 236388-66-2 (3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside 

Relevant academic research and scientific papers

Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide

The C-sulfatide 1b was synthesized through a [2,3]-Wittig sigmatropic rearrangement and a Horner-Wadsworth-Emmons olefination as the key steps. The C-analogue 1b is less immunogenic than natural sulfatide 1a, but induces a preferential secretion of the proinflammatory cytokine IFN-γ.

Stereoselective synthesis of the C-linked analogue of β-D-galactopyranosyl-L-serine

The coupling of the D-serinal derivative 7 with the D-galactopyranosylmethylene phosphorane generated from the phosphonium salt 6 and reduction of the resulting alkene led to the C-glycosylated amino alcohol 9 that in turn was oxidized to the title amino acid in 44% overall yield.