Benzyloxy hydrogenolysis

Inosine, 6-benzyloxy-9- -D-ribofuranosyl-2-dimethylamino-hydrogenolysis, 5, 558 Inosine, 2 -deoxy-alkylation, 5, 538 Inosine, 6-phenacylthio-dethiation, S, 559 Inosine 5 -monophosphate biosynthesis, 1, 88 Inosines, thio-synthesis, 5, 584 Inositol, D-l,4-anhydro-synthesis, 1, 416 Inositols synthesis, 1, 416 Insecticides... 

The benzyloxy group on a /3-lactam nitrogen was cleaved by hydrogenolysis (H2, Pd-C) or by TiCl3 [MeOH, H2O, (NH4)2C03, Na2C03]. ... 

Debenzylation of the benzyloxy groups in 156 and 158 to 157 and 159 respectively was achieved, without affecting the aromaticity of the system, by catalytic hydrogenolysis in the presence of palladium-on-charcoal (86TL3127 89JHC991) (Scheme 61). 

The deprotection of the Cbz protected amino acid proceeds via a two step mechanism (Figure 1). The first step comprises the catalytic hydrogenolysis of the benzyloxy group of the Cbz-protected amino acid (1). Toluene (3) is formed from the O-benzyl group as well as an unstable carbamic acid intermediate (2). This intermediate decomposes to form the unprotected amino acid (4) and carbon dioxide (5). 

Selective removal of the benzyl ether-protecting group without hydrogenolysis of the ketal C-O bonds was performed on Ra-Ni in EtOH.154 155 A solution of benzyloxy acetal in MeOH with 5% Pd/C was stirred at room temperature with a H2 pressure from a balloon until the reaction was complete (Scheme 4.30).156... 

Both benzyl-oxygen and nitrogen-oxygen bonds undergo hydrogenolysis readily in the presence of a benzyloxy-nitrogen bond but it appears that the benzyl-oxygen bond can be made to cleave selec-... 

Many organic reactions can be conducted very rapidly under microwave irradiation. Microwave-induced organic reaction enhancement chemistry techniques were used for the rapid formation of an ot-benzyloxy-p-lactam (10 in Fig. 4.2) and the hydrogenolysis of its benzyloxy group on a few-gram scale in 1-5 minutes with HC02NH4 and Pd/C in ethylene glycol as the reaction medium in a domestic microwave oven.243... 

Both benzyl-oxygen and N-O bonds can undergo hydrogenolysis in the compounds containing benzyloxy-nitrogen bonds,... 

AUylic ethers were reduced by treatment with lithium in ethylamine to alkenes [636]. Benzyl ethers are hydrogenolyzed easily, even more readily than benzyl alcohols [637], 3,5-Bis(benzyloxy)benzyl alcohol gave 3,5-dihydroxy-benzyl alcohol on hydrogenation over palladium on carbon at room temperature and atmospheric pressure in quantitative yield [638. Hydrogenolysis of benzylic ethers can also be achieved by refluxing the ether with cyclohexene (as a source of hydrogen) in the presence of 10% palladium on carbon in the presence of aluminum chloride [639]. 

Purine, 6-amino-2-benzyloxy-9-methyl-hydrogenolysis, 5, 558 Purine, 2-amino-6-chloro-reactions, 5, 562 Purine, 6-amino-2,8-dichloro-hydrogenolysis, 5, 563... 

---