ammonium cerium(IV) nitrate; silica gel 1) MeOH, 5-10 deg C 2) benzene, reflux; Yield given. Multistep reaction;

1.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C 2.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 3.1: 90 percent / potassium carbonate / methanol 4.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 4.2: tetrahydrofuran / -78 °C 5.1: TFA / CH2Cl2 / 10 h View Scheme

[NEt3Me]I; water; dihydrogen peroxide in acetonitrile T=55°C; 15 h;

1.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C 2.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 3.1: 90 percent / potassium carbonate / methanol 4.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 4.2: tetrahydrofuran / -78 °C 5.1: TFA / CH2Cl2 / 10 h 6.1: potassium carbonate / acetone View Scheme

ammonium cerium (IV) nitrate in methanol T=20°C; 4 h; Inert atmosphere;

 in  methanol  

With  phosphate buffer; E. coli BL21(DE3) harboring pACRGD plasmid cell-free extract; nicotinamide adenine dinucleotide phosphate; D-glucose in  water T=30°C; pH=7.0;