138552-47-3

Upstream product

• 1623-08-1 phosphoric acid dibenzyl ester 
• 131897-73-9 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl bromide 
• 180476-30-6 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl-1-trichloroacetoimidate 
• 180476-31-7 ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 64913-16-2 L-fucose tetraacetate 
• 98-88-4 benzoyl chloride 
• 69558-02-7 Ethyl 2,3,4-tri-O-acetyl-1-thio-α/β-L-fucopyranoside 
• 93-97-0 benzoic acid anhydride 
• 140223-15-0 (3S,4R,5R,6S)-6-methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate 
• 119095-47-5 triethylammonium dibenzyl phosphate 

Downstream Products

• 62012-79-7 dTDP-β-L-fucose 
• 149300-28-7 C₂₇H₂₅O₁₁P 
• 16562-59-7 β-L-Fucopyranosyl phosphate 

Relevant academic research and scientific papers

Exploiting nucleotidylyltransferases to prepare sugar nucleotides

(Graph Presented) Enzymatic approaches to prepare sugar nucleotides are gaining in importance and offer several advantages over chemical synthesis including high yields and stereospecificity. We report the cloning, expression, and purification of two new wild-type thymidylyltransferases and observed catalysis with a wide variety of substrates. Significant product inhibition was not observed with the enzymes studied over a 24 h period, enabling the efficient preparation of 15 sugar nucleotides, clearly demonstrating the synthetic utility of these biocatalysts.

Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides

As Leloir glycosyltransferases are increasingly being used to prepare oligosaccharides, glycoconjugates, and glycosylated natural products, efficient access to stereopure sugar nucleotide donor substrates is required. Herein, the rapid synthesis and purification of eight sugar nucleotides is described by a facile 30 min activation of nucleoside 5′-monophosphates bearing purine and pyrimidine bases with trifluoroacetic anhydride and N-methylimidazole, followed by a 2 h coupling with stereospecifically prepared sugar-1-phosphates. Tributylammonium bicarbonate and tributylammonium acetate were the ion-pair reagents of choice for the C18 reversed-phase purification of 6-deoxysugar nucleotides, and hexose or pentose-derived sugar nucleotides, respectively.

One-step, stereocontrolled synthesis of glycosyl 1-phosphates, uridine- 5'-diphosphogalactose, and uridine-5'-diphosphoglucose from unprotected glycosyl donors

The reaction of 2-(1,2-trans-glycopyranosyloxy)-3-methoxypyridines (MOP glycosides) with phosphoric acid leads to the corresponding 1,2-cis-1- phosphates in good yield and excellent stereoselectivity. 1-Phosphate esters of α-D-glucopyranose, α-D-galactopyranose, and 2-azido-2-deoxy-α-D- galactopyranose were thus prepared without recourse to protective groups. In the L-fucose series, the major product was the α-L-fucosyl 1-phosphate. An alternative method that relies on neighboring group participation allowed the preparation of a protected β-L-fucosyl 1-phosphate. Reaction of unprotected β-D-glucopyranosyloxy and β-D-galactopyranosyloxy MOP donors with uridine diphosphoric acid gave UDP-Glc and UDP-Gal with preponderance of the desired α-anomeric configuration.

Synthesis of guanosine 5′-(β-L-fucopyranosyl)-diphosphate revisited

It will be demonstrated that a successful synthesis of β-L-fucopyranose-1-phosphate (2), a key intermediate in the preparation of guanosine 5′-(β-L-fucopyranose)-diphosphate (1), strongly depends on the nature of the acyl protecting groups for the non-anomeric hydroxyl functions. Thus, the perbenzoylated, instead of peracetylated, α-L-fucopyranosyl trichloroacetimidate (11) or the corresponding ethyl β-thiofucopyranoside proved to be a convenient starting compound for the preparation of 2. Further, condensation of N,N'-dicyclohexyl-4-morpholinecarboxamidinium guanosine 5′-morpholidophosphate with excess 2 gave the title compound without concomitant formation of bisguanosine-5′-diphosphate (16).

Large-scale synthesis of β-L-fucopyranosyl phosphate and the preparation of GDP-β-L-fucose

A practical 15-mmol large-scale synthesis of β-L-fucopyranosyl dicyclohexylammonium phosphate from L-fucose in 63percent overall yield was developed.The synthesis took advantage of a neighboring Bz-2 group participating in a Koenigs-Knorr like glycosylati

An approach towards the synthesis of 1,2-trans glycosyl phosphates via iodonium ion assisted activation of thioglycosides

Phosphorylation of benzoylated ethyl 1,2-trans 1-thioglycosides with dibenzyl phosphate in the presence of NIS gave, after removal of all protecting groups, 1,2-trans glycosyl phosphates. The scope of the stereoselective method was demonstrated by the syn