254757-67-0

Upstream product

• 106-95-6 allyl bromide 
• 254757-73-8 (2S,5R)-6-Benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-hexanoic acid 

Downstream Products

• 270913-32-1 (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine allyl ester 
• 270089-67-3 (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine 
• 623574-45-8 (5R)-N^α-[(fluoren-9-yl)methoxycarbonyl]-N^ε-benzyloxycarbonyl-5-O-(2,3,6-tri-O-acetyl-4-O-methyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine allyl ester 

Relevant academic research and scientific papers

9-BBN as a convenient protecting group in functionalisation of hydroxylysine

9-BBN was used for regioselective protection of the α-amino and α-carboxyl groups of (5R)-5-hydroxy-L-lysine. The resulting 9-BBN complex was then employed in transformations such as N-Cbz protection, azido transfer, O-glycosylation, and O-silylation. Further manipulations led to improved methods for preparation of hydroxylysine and galactosylated hydroxylysine building blocks, suitable for direct use in peptide synthesis under standard Fmoc conditions.

An improved synthesis of a galactosylated hydroxylysine building block and its use in solid-phase glycopeptide synthesis

Different protective groups for (5R)-5-hydroxy-L-lysine were investigated in silver silicate promoted glycosylations with aceto- bromogalactose as glycosyl donor. Best results were obtained with Fmoc- Hyl(Cbz)-OAll, which was glycosylated in 80% yield. Re