1: 87.5 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 2: hydrogen / Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C 3: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C 4: CH2Cl2 / 0 - 20 °C 5: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 6: 55 percent / dimethyldioxirane / CH2Cl2; acetone / -30 - 20 °C View Scheme

1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C 2: 87.5 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 3: hydrogen / Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C 4: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C 5: CH2Cl2 / 0 - 20 °C 6: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 7: 55 percent / dimethyldioxirane / CH2Cl2; acetone / -30 - 20 °C View Scheme

1: 95 percent / DCC 2: 84 percent / H2 / Ra-Ni 3: 1.) 2,4,6-trichlorobenzoyl chloride, iPr2NEt, 2.) HCl, 3.) O-benzotriazol-1-yl-N,N,N',N'-bis(pentamethylene)uroniumhexafluorophosphate, 4.) Bu4NF 4: 63 percent / Me3SiCl 5: 63 percent / PPh3 / H2O 6: 98 percent / K2CO3 / acetone View Scheme

1: CH2Cl2 / 0 - 20 °C 2: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 3: 55 percent / dimethyldioxirane / CH2Cl2; acetone / -30 - 20 °C View Scheme

1: 1.) lithium diisopropylamide / 1.) THF, hexanes, -60 deg C, 10 min, 2.) THF, hexanes, 5 deg C, 15 min 2: phosphate buffer, sodium azide / H2O / 120 h / 25 °C / 2-propanol-treated Candida rugosa lipase presence, pH 7.0 3: 95 percent / diisobutylaluminum hydride / diethyl ether; hexane / 3 h / -75 - -70 °C 4: 18 percent / zinc-lead, iodine / diethyl ether; benzene / 0.5 h / Heating 5: 74 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 23 deg C, 16 h 6: CH2Cl2 / 2 h / 23 °C 7: 32 mg / pentafluorophenyl diphenylphosphinate, diisopropylethylamine / dimethylformamide / 16 h / 23 °C 8: 26 mg / m-chloroperoxybenzoic acid / CH2Cl2 / 23 °C View Scheme

1: phosphate buffer, sodium azide / H2O / 120 h / 25 °C / 2-propanol-treated Candida rugosa lipase presence, pH 7.0 2: 95 percent / diisobutylaluminum hydride / diethyl ether; hexane / 3 h / -75 - -70 °C 3: 18 percent / zinc-lead, iodine / diethyl ether; benzene / 0.5 h / Heating 4: 74 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 23 deg C, 16 h 5: CH2Cl2 / 2 h / 23 °C 6: 32 mg / pentafluorophenyl diphenylphosphinate, diisopropylethylamine / dimethylformamide / 16 h / 23 °C 7: 26 mg / m-chloroperoxybenzoic acid / CH2Cl2 / 23 °C View Scheme

1: 90 percent / morpholine, tetrakis(triphenylphosphine)palladium / tetrahydrofuran / 1 h / 23 °C 2: 74 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 23 deg C, 16 h 3: CH2Cl2 / 2 h / 23 °C 4: 32 mg / pentafluorophenyl diphenylphosphinate, diisopropylethylamine / dimethylformamide / 16 h / 23 °C 5: 26 mg / m-chloroperoxybenzoic acid / CH2Cl2 / 23 °C View Scheme

1: 18 percent / zinc-lead, iodine / diethyl ether; benzene / 0.5 h / Heating 2: 74 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 23 deg C, 16 h 3: CH2Cl2 / 2 h / 23 °C 4: 32 mg / pentafluorophenyl diphenylphosphinate, diisopropylethylamine / dimethylformamide / 16 h / 23 °C 5: 26 mg / m-chloroperoxybenzoic acid / CH2Cl2 / 23 °C View Scheme

1: 95 percent / diisobutylaluminum hydride / diethyl ether; hexane / 3 h / -75 - -70 °C 2: 18 percent / zinc-lead, iodine / diethyl ether; benzene / 0.5 h / Heating 3: 74 percent / 4-dimethylaminopyridine, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 23 deg C, 16 h 4: CH2Cl2 / 2 h / 23 °C 5: 32 mg / pentafluorophenyl diphenylphosphinate, diisopropylethylamine / dimethylformamide / 16 h / 23 °C 6: 26 mg / m-chloroperoxybenzoic acid / CH2Cl2 / 23 °C View Scheme

1.1: 93 percent / DMAP; EDC; Et3N / CH2Cl2 / 31 h / 0 - 20 °C 2.1: aq. TFA / CH2Cl2 / 0 - 20 °C 3.1: 77 percent / HATU; DIPEA / dimethylformamide / 1.5 h / 0 - 20 °C 4.1: (CH3O)3CH; PPTS / CH2Cl2 / 2 h / 20 °C 4.2: AcBr / CH2Cl2 / 4 h / 20 °C 4.3: 72 percent / KHCO3; (nBu)4NBr / 1,2-dimethoxy-ethane / 27 h / 40 °C View Scheme