86061-06-5

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 73731-37-0 Fmoc-Thr-OH 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 117088-31-0 O-tert-butyl-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester 

Downstream Products

• 141462-10-4 N^α-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine pentafluorophenyl ester 
• 132914-78-4 N^α-(fluoren-9-ylmethoxycarbonyl)-O-<3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl>-L-threonine pentafluorophenyl ester 
• 145491-21-0 N^α-(fluoren-9-ylmethoxycarbonyl)-3-O-<2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>3)-4,6-di-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl>-L-threonine pentafluorophenyl ester 
• 140684-85-1 C₅₆H₇₇N₉O₁₅S₂ 
• 151145-33-4 N^α-(Fluoren-9-ylmethoxycarbonyl)-O-<3,4,6-tri-O-acetyl-2-O-<2,3,4-tri-O-benzoyl-6-O-bis-(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranosyl>-α-D-mannopyranosyl>-L-threonine pentafluorophenyl Ester 
• 160410-56-0 N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester 
• 162894-85-1 N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-threonine pentafluorophenyl ester 
• 168139-79-5 N-(9-fluorenylmethoxycarbonyl)-O-<2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>3)-4-O-acetyl-2-azido-6-O-benzoyl-2-deoxy-α-D-galactopyranosyl>-L-threonine pentafluorophenyl ester 
• 174004-29-6 (2S,3R)-3-[(2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid pentafluorophenyl ester 
• 188397-31-1 N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester 

Relevant academic research and scientific papers

Removal of acyl protective groups from glycopeptides: Base does not epimerize peptide stereocenters, and β-elimination is slow

Epimerization of glycopeptide stereocenters and β-elimination have been considered as important potential side reactions on deacylation of glycopeptides which have the carbohydrate moieties protected with O-acyl groups. Since no systematic investigation of these side reactions has been reported, a model acetylated, O-linked glycotripeptide and its three epimers at the α-carbon stereocenters were prepared. The model glycopeptide did not undergo any epimerization (1H NMR spectroscopy, under various conditions which are in common use for deacetylation of glycopeptides. Under more severe conditions, which are required for removal of O-benzoyl groups, β-elimination occurred slowly and was accompanied by slight (5%) epimerization. The surprisingly low tendency of glycopeptides to undergo base catalyzed epimerization and β-elimination is most likely due te protection of the α-carbon stereocenters by deprotonation of the adjacent amide groups.

Syntheses of TN building blocks Nα-(9- fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D- galactopyranosyl)-L-serine/L-threonine pentafluorophenyl esters: Comparison of protocols and elucidation of side reactions

TN antigen building blocks Nα-(9- fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d- galactopyranosyl)-l-serine/l-threonine pentafluorophenyl ester [Fmoc-l-Ser/l-Thr(Ac3-α-d-GalN3)-OPfp, 13/14]

Convenient Synthesis of O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-serine and -threonine Building Blocks for Solid-phase Glycopeptide Assembly

The suitably protected building blocks for solid-phase glycopeptide synthesis, Nα-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp, 11, and Nα-Fmoc-Thr(Ac3-β-D-GlcNAc)-OPfp, 12, have been synthesized by stereoselective glycosidation of the 2-allyloxycarbonylamino glycosyl donor 7 with Nα-Fmoc-Ser-OPfp, 3, and Nα-Fmoc-Thr-OPfp, 4, followed by Pd0-catalysed allyl transfer from the N-allyloxycarbonyl group in the presence of acetic anhydride.

The active ester N-fmoc-3-O-[Ac4-α-D-Manp-(1→2)-Ac 3-α-D-Manp-1-]=thre-O-Pfp as a building block in solid-phase synthesis of an o-linked dimannosyl glycopeptide

The active ester Nα-Fmoc-3-O-[Ac4-α-D-Manp-(1→2)-Ac 3-α-D-Manp-1-]-Thr-O-Pfp (6) was synthesized by direct condensation of Ac4-α-D-Manp-(1→2)-Ac3-α-D-Manp-Br (4) with Fmoc-Thr-O-Pfp (5) and used as a building block in an automated continuous-flow solid-phase synthesis of an O-glycosylated heptadeca amino acid fragment of the insulin-like growth factor 1 (IGF-1).

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.