195147-46-7

Upstream product

• 157477-49-1 (R/S)-but-3-en-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 200396-09-4 ((Ξ)-1-methyl-allyl)-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 195147-45-6 but-3-en-2-yl 4,6-O-benzylidene-β-D-glucopyranoside 

Downstream Products

• 195147-51-4 dibenzyl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranosyl phosphate 
• 1054675-46-5 Trifluoro-methanesulfonic acid (2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(1-methyl-allyloxy)-tetrahydro-pyran-3-yl ester 
• 195147-49-0 (E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside 
• 195147-47-8 (R/S)-but-3-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside 

Relevant academic research and scientific papers

Preparation of fluorinated galactosyl nucleoside diphosphates to study the mechanism of the enzyme galactopyranose mutase

A novel latent→active phosphorylation strategy has been employed for the preparation of two fluorinated nucleoside diphosphates (compounds I and II). The strategy is based on the isomerisation of substituted allyl to vinyl glycosides which were subsequently phosphorylated by treatment with dibenzyl hydrogen phosphate, N-iodosuccinimide and a catalytic amount of trimethylsilyl triflate. This methodology is very suitable for the preparation of nucleoside diphosphates that have a modification in the saccharide moiety since the allyl moiety serves first as an anomeric protecting group, allowing for protecting-group manipulation and functionalisation of the sugar ring, but after isomerisation to the corresponding vinyl glycoside it acts as an anomeric leaving group. The 2-F and 4-F Gal-UDP derivatives I and II do not inhibit the enzyme galactopyranose mutase in the direction pyranose → furanose but both compounds have been found to inhibit the reverse reaction.