116546-90-8

Upstream product

• 64913-16-2 L-fucose tetraacetate 
• 69558-02-7 Ethyl 2,3,4-tri-O-acetyl-1-thio-α/β-L-fucopyranoside 
• 98-88-4 benzoyl chloride 

Downstream Products

• 16562-59-7 β-L-Fucopyranosyl phosphate 
• 137063-50-4 C₅₅H₅₄O₁₃ 
• 137063-48-0 C₅₅H₅₄O₁₃ 

Relevant academic research and scientific papers

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).

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