Total Synthesis of a Linear Tetrasaccharide Repeating Unit of Vibrio vulnificus MO6-24

Total Synthesis of the Conjugation-Ready Tetrasaccharide Repeating Unit of Shewanella japonica Type Strain KMM 3299T

“…We began our synthesis with construction of orthogonally protected rare sugar l -fucosamine acceptors and 4-azido- d -fucose donor, as shown in Scheme . For the synthesis of L-fucosamine building blocks, we started with the known l -fucosamine 10 , which upon benzylation of C4-OH using BnBr and NaH followed by oxidative denaphthylmethylation using DDQ afforded l -fucosamine acceptor 8 in 71% yield. The C4-OH group of l -fucosamine was protected with a benzyl group so as to reduce the number of deprotection steps for efficient synthesis.…”