352020-76-9

Upstream product

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 848844-32-6 (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-galacto-oct-2-enitol 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 1826-67-1 vinyl magnesium bromide 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 

Downstream Products

• 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 
• 144634-18-4 methyl (2S)-2-(tert-butoxycarbonylamino)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-butanoate 
• 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 
• 906545-88-8 (3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-4-hydroxy-5-nonadecene 
• 906545-87-7 (3S,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-4-oxo-5-nonadecene 
• 906545-86-6 dimethyl [(3S)-5-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-2-oxo-pentyl]phosphonate 
• 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 

Relevant academic research and scientific papers

Stereoselective glycosylation of exo-glycals by microwave-assisted Ferrier rearrangement

exo-Glycosyl carbonates were shown to be efficient glycosyl donors in microwave-assisted glycosylation. In these reactions α-glycosyl additions occurred with excellent stereoselectivity and were complete in 4-8 min with 75-92% yield. Interestingly exo-glycals were found to have higher activity than endo-glycals and common glycosides, the reactions of which can be improved by the addition of Lewis acid to result in a higher yield and enhanced stereoselectivity.

Reinvestigation of the synthesis of per-benzylated glycosylethenes: A new result

Addition of vinylmagnesium bromide on the perbenzylated glucono-1, 5-lactone gave, after reduction with Et3SiH/BF3· Et2O, a mixture of the desired β-C-vinyl glucoside 1 and the unexpected β-C-but-3-enyl glucoside 3 resulting from double addition of vinylmagnesium bromide on the lactone. Similar results have been obtained with the perbenzylated galactono-1,5-lactone. This side reaction was then been explored to prepare β-C-but-3-enyl glycosides and other β-C-glycosyl derivatives by employing different Grignard reagents. An alternative approach to the per-benzylated glycosylethenes has been studied and compared.

A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded α-stereoselect