1: n-octadecanoic acid chloride With pyridine in 1-methyl-pyrrolidin-2-one T=20°C; 2: (4R,3S,2S)-2-aminooctadecane-1,3,4-triol in tetrahydrofuran T=20°C; Further stages.;

Novozym 435 T=120°C; 4 h; Enzymatic reaction; Kinetics;

1.1: trifluoromethanesulfonyl azide; potassium carbonate; copper(II) sulfate / methanol; H2O; CH2Cl2 / 3 h / 20 °C 2.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2; dimethylformamide / 24 h / 20 °C 3.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 4.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 5.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 5.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 92 percent / TEA / tetrahydrofuran / 0.5 h / 20 °C 2: 97 percent / pyridine / dimethylformamide / 0.5 h / -40 °C 3: 99 percent / Ac2O; DMSO / 16 h / 20 °C 4: 89 percent / KHMDS / tetrahydrofuran; toluene / 3 h / -68 - -20 °C 5: 91 percent / HCOOH; TEA / Pd(OAc)2(triphenylphosphine)2 / dimethylformamide / 4 h / 60 °C 6: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 0 °C View Scheme