169061-79-4

Upstream product

• 122210-05-3 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 

Downstream Products

• 160067-63-0 N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine 

Relevant academic research and scientific papers

Preparation of Building Blocks for Glycopeptide Synthesis by Glycosylation of Fmoc Amino Acids Having Unprotected Carboxyl Groups

Nα-Fmoc amino acids with an unprotected α-carboxyl group have been glycosylated with carbohydrate 1,2-trans peracetates using Lewis acids as promoters.Aliphatic and phenolic O- and S-glycosides of amino acids, with a 1,2-trans anomeric configuration, were obtained as products in 34-65percent yields.The glycosylated building blocks have the protective groups of choice (i.e.O-acetyl and Nα-Fmoc) for direct use in stepwise synthesis of glycopeptides.The starting materials are readily available and the method does not require an extensive experience in synthetic carbohydrate chemistry.

Glycosylation with N-Troc-protected glycosyl donors

N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside. The N-Troc-protected donors gave pure β-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups.