180476-31-7

Upstream product

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

Downstream Products

• 116546-91-9 C₅₅H₅₄O₁₃ 
• 180476-30-6 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl-1-trichloroacetoimidate 
• 16562-59-7 β-L-Fucopyranosyl phosphate 
• 138552-47-3 dibenzyl 2,3,4-tri-O-benzoyl-β-L-fucopyranosyl 1-phosphate 

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).