Fluoren-9-ylmethoxycarbonyl

YH Wang, JC Xu. One-pot liquid-phase synthesis of DSIP and 5-DSIP using fluoren-9-ylmethoxycarbonyl-protected amino acid pentafluorophenyl esters. (3-diethylami-nopropane-2-ol) Synthesis 845, 1990. 

V -(Fluoren-9-ylmethoxycarbonyl)-0-[0-(3,4,6-tri-0-acetyl-2-azido-2-deoxy-a-D-galactopyranosyl)-(1 3)-(4,6-di-0-acetyl-2-azido-2-deoxy-a-D-galactopyranosyl)]-L-threonine Pentafluorophenyl Ester... 

V"-Fluoren-9-ylmethoxycarbonyl-3-0- 2-acetamido-2-deoxy-3,4-0-isopropyKdene-6-0-[methyl(5-acet-amido-4,7,8,9-tetra-0-acetyl-3,5,-dideoxy-D-glycero-a-galacto-2-nonulopyranosyl)onate]-a-D-galacto-pyranosylJ-L-threonme Benzyl Ester (84) 11251... 

Scheme 4.13 (a)). They used a similar backbone to that found in the Denkewalter lysine-based series,f4 but employed A 1,N -di(fluorene-9-ylmethoxycarbonyl)-L-lysine benzotri-azole (39) as the activated ester building block for tier construction (Scheme 4.13 (b)). After acylation and subsequent deprotection, the two-step process was repeated. Each tier was terminally functionalized with the preformed benzotriazole ester of chloroace-tylglycylglycine, followed by reaction with peracetylated 2-thiosialic acid. Removal from the solid state support, followed by hydrolysis, afforded the desired inhibitor (e.g., 38) in nearly quantitative yield. 

Diels-Alder reaction with support-bound 4-[3-(tert-butyldimethylsilyloocy)buta-l,3-die-nyl] groups (Scheme 65) [310] N-[(Fluoren-9-ylmethoxycarbonyl)ethyl]maleimide (304) (135 mg, 0.375 mmol) was weighed into a screw-cap vial (Reacti-Vial) and toluene (800 pL) was added. The vial was sealed and heated until the dienophile dissolved, and resin bearing a diene (302 or 306) was added and allowed to swell in reagent and solution. The vial was sealed and kept at 110 °C overnight The reaction solution was drained and the resin washed as follows ... 

The syntheses of Boc- and Fmoc (97/-fluoren-9-ylmethoxycarbonyl)-protected (2S,4R)- and (25, 45)-fluoroprolines from (25, 31 )-hydroxyproline have been reported. " This synthesis featured a Mitsunobo inversion of the hydroxyproline and fluorination with DAST. A similar synthesis was reported that used morpholinosulfur trifluoride as the fluorinating agent. 

Two recently reported alkoxycarbonyl protecting groups for alcohols are fluoren-9 ylmethoxycarbonyl (FmOC) and 2-(triphenylphosphonio)ethoxy-carbonyl (PeOC). Both groups are removed by elimination mechanisms the FmOC derivatives (49) are cleaved by triethylamine in pyridine and the PeOC group is removed from protected alcohols (50) by dimethylamine in methanol. 

Mell997b Mellor, S.L. and Chan, W.C., 4-[2,4-Dimethoxy-phenyl(N-fluoren-9-ylmethoxycarbonyl-N-alkylaminooxy)-me-thyllphenoxymethlyl polystyrene A Multiple Solid-Phase Approach to N-Alkylhydroxamic Acids, J. Chem. Soc., Chem. Commun., (1997) 2005-2006. 

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