1: protected as tetrahydropyranyl ether 2: 84 percent / TBAF 3: 98 percent / deacylation 4: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature 5: diisobutyl aluminum hydride 6: 2.) aq. acetic acid View Scheme

Multi-step reaction with 5 steps 1: protected as tetrahydropyranyl ether2: 84 percent / TBAF3: 98 percent / deacylation4: 73 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature5: diisobutyl aluminum hydride  

Multi-step reaction with 3 steps 2: Pd(MeCN)2Cl2 / tetrahydrofuran / 2 h / Ambient temperature3: NaBH4  

Multi-step reaction with 2 steps 1: Pd(MeCN)2Cl2 / tetrahydrofuran / 2 h / Ambient temperature2: NaBH4  

With  sodium tetrahydroborate