A convenient protocol for the deprotection of N-benzyloxycarbonyl (Cbz) and benzyl ester groups

Synthesis of Aminomethylene-gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism

“…1 H NMR (400 MHz, CDCl 3 ): δ 7.42–7.23 (m, 10H, CH Ar ), 5.47 (s, 1H, NH), 5.11 (q, J = 12.2 Hz, 2H, OCH 2 Ph), 4.86 (s, 1H, CH), 3.95–3.80 (m, 2H, CH 2 OH). Data in accordance with the literature …”

“…The title compound (3.76 g, 13.87 mmol, 95% yield) was obtained as a white powder following the procedure described by Sultane et al from commercially available l -phenylglycinol (2.00 g, 14.58 mmol). R f petroleum ether/EtOAc (6/4, v/v): 0.26.…”

“…13 Benzyl (S)-(2-Hydroxy-1-phenylethyl)carbamate (1a). The title compound (3.76 g, 13.87 mmol, 95% yield) was obtained as a white powder following the procedure described by Sultane et al 54 from commercially available L-phenylglycinol (2.00 g, 14.58 mmol). R f petroleum ether/EtOAc (6/4, v/v): 0.26.…”

“…Data in accordance with the literature. 54 Benzyl (S)-(1-Hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (1d). The title compound (720 mg, 2.22 mmol, 42% yield) was obtained as a white foam following the procedure from Yeung et al 55 from the commercially available L-tryptophanol (1.00 g, 5.26 mmol).…”

Indium-, Magnesium-, and Zinc-Mediated Debenzylation of Protected­ 1H-Tetrazoles: A Comparative Study

“…The benzyl moiety is commonly used in synthetic organic chemistry as protecting group for heteroatoms (O, S, N), mainly due its easy introduction and inherent stability. 1 Concerning the corresponding deprotection, the hydrogenolysis has been widely used in multistep organic synthesis, particularly for the debenzylation of N-benzylamines, 2 benzyl ethers, 3 benzyl esters, 4 and benzyl carbamates. 5 This methodology has also been used for the debenzylation of nitrogen-containing heterocycles.…”