W-4 Raney-Ni in ethanol Ambient temperature;

1: With (S)-p-Tol-BINAP; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane in toluene T=0°C; 12 h; 2: With tetrabutyl ammonium fluoride; water in tetrahydrofuran; diethyl ether; toluene 1 h; 3: With E. coli expressing cyclohexanone monooxygenase; LB-Ampicillin medium; isopropyl 1-thio-β-D-galactopyranoside; D-glucose in glycerol T=30°C; Baeyer-Villiger oxidation; Title compound not separated from byproducts;

1: 1.) mCPBA; 2.) trifluoroacetic anhydride / 1.) CH2Cl2, 0 deg C, 1 h; 2.) 0 deg C -> r.t., overnight 2: 80 percent / diethyl ether / 0.5 h / -20 - -17 °C 3: 76 percent / W-4 Raney nickel / ethanol / Ambient temperature; 1-3 h View Scheme

1: 80 percent / diethyl ether / 0.5 h / -20 - -17 °C 2: 76 percent / W-4 Raney nickel / ethanol / Ambient temperature; 1-3 h View Scheme

1: 1) diisopropylamine, butyllithium / 1) THF, hexane, 78 deg C, 10 min, 2) THF, HMPA, to r.t. in 10 h 2: 1.617 g / mCPBA / CH2Cl2 / 0.5 h 3: 98 percent / trifluoroacetic anhydride / CH2Cl2 / 12 h 4: 1) Cu(I)I / 1) hexane, 2) THF 5: 76 percent / W-4 Raney-Ni / ethanol / Ambient temperature View Scheme

1: 98 percent / trifluoroacetic anhydride / CH2Cl2 / 12 h 2: 1) Cu(I)I / 1) hexane, 2) THF 3: 76 percent / W-4 Raney-Ni / ethanol / Ambient temperature View Scheme

2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; tetrakislt;iodo(tri-n-butylphosphine)gt;copper(I); 1,2:5,6-di-O-isopropylidene-3-deoxy-3-thio-α-D-glucofuranose in diethyl ether; hexane Yield given. Yields of byproduct given;

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copper(l) iodide 1) hexane, -40 deg C; Yield given. Multistep reaction;