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-Reference-Cited by-同舟云学术

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

Published:1986-01 Issue:31 Volume:27 Page:3651-3654
ISSN:0040-4039
Container-title:Tetrahedron Letters
language:en
Short-container-title:Tetrahedron Letters

Author:

Tanaka Tatsuyoshi,Oikawa Yuji,Hamada Tatsuo,Yonemitsu Osamu

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference27 articles.

1. Specific removal of o-methoxybenzyl protection by DDQ oxidation.

2. Protection of hydroxy groups by intramolecular oxidative formation of methoxybenzylidene acetals with DDQ

3. Kinetic acetalization for 1,2- and 1,3-diol protection by the reaction of p-methoxyphenylmethyl methyl ether with DDQ

4. DMPM (3,4-dimethoxybenzyl) protecting group for hydroxy function more readily removable than MPM (P-methoxybenzyl) protecting group by DDQ oxidation

5. 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

Cited by 54 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Oxidative Deprotection of Benzyl Protecting Groups for Alcohols by an Electronically Tuned Nitroxyl-Radical Catalyst;The Journal of Organic Chemistry;2023-08-16

2. Advances in the Synthesis of Natural Products and Medicinally Relevant Molecules from Glycals;ChemistrySelect;2022-10-25

3. Oxidative Deprotection of p-Methoxybenzyl Ethers by a Nitroxyl Radical Catalyst;YAKUGAKU ZASSHI;2021-10-01

4. Highly Diastereo‐ and Enantioselective Synthesis of 3,6′‐Bisboryl‐ anti ‐1,2‐oxaborinan‐3‐enes: An Entry to Enantioenriched Homoallylic Alcohols with A Stereodefined Trisubstituted Alkene;Angewandte Chemie International Edition;2020-11-10

5. Highly Diastereo‐ and Enantioselective Synthesis of 3,6′‐Bisboryl‐ anti ‐1,2‐oxaborinan‐3‐enes: An Entry to Enantioenriched Homoallylic Alcohols with A Stereodefined Trisubstituted Alkene;Angewandte Chemie;2020-11-10