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Selective hydrogenolysis of the benzyl protecting group for hydroxy function with raney nickel in the presence of the MPM (4-methoxybenzyl) and DMPM (3,4-dimethoxybenzyl) protecting groups

✍ Scribed by Yuji Oikawa; Tatsuyoshi Tanaka; Kiyoshi Horita; Osamu Yonemitsu

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 201 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)91294-8

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✦ Synopsis

The benzyl protecting group for hydroxy function was selectively removed by catalytic hydrogenolysis with Raney nickel in the presence of the MPM (4-methoxybenzyl) and DMPM (3,4-dimethoxybenzyl)protecting groups, and applied to the synthesis of some synthons to macrolide and polyether antibiotics.

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Total synthesis of tylonolide, the aglyc

Total synthesis of tylonolide, the aglycone of the 16-membered ring macrolide tylosin, from D-glucose. Selective application of MPM and DMPM protecting groups for hydroxy functions

✍ Tatsuyoshi Tanaka; Yuji Oikawa; Tatsuo Hamada; Osamu Yonemitsu 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 286 KB

Segments i (Cll-C17) and ii (Cl-ClO), synthesized from D-glucose by employing some stereoselective reactions and benzyl-type protecting groups, were esterified and cyclized to the 16-membered enone, which was readily converted to tylonolide, the aglycone of tylosin. Tylosin is a typical 16-membered