An efficient and selective deprotecting method for methoxymethyl ethers

Synthetic Communications

Volumn 34, Issue 23, 2004, Pages 4325-4330

  Peng, Yungui ^a   Ji, Changyun ^a   Chen, Yingchun ^b   Huang, Chengzhi ^a   Jiang, Yaozhong ^b  

^a SOUTHWEST UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Deprotecting; Methoxymethyl; Selectively

Indexed keywords

ETHER DERIVATIVE; METHOXYMETHYL ETHER DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

EID: 10644288501     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200039382     Document Type: Article

References (15)

1. Schelhaas, M.; Waldmann, H. Protecting group strategies in organic synthesis. Angew. Chem., Int. Ed. Engl. 1996, 35, 2056.
2. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis; Wiley: New York, 1991; Chap. 2, 5.
3. Kocienki, P.J. Protective Groups; Georg Thieme: New York, 1994.
4. Auerbach, J.; Weinreb, S.M. Synthesis of Terrein, a metabolite of aspergillus terreus. J. Chem. Soc., Chem. Commun. 1974, 298.
5. Meyers, A.I.; Durandetta, J.L.; Munavu, R. 2-Thiazolines in organic synthesis. Formation of beta-hydroxy aldehydes with protected hydroxy groups. Synthesis of homoallylic alcohols. J. Org. Chem. 1975, 40, 2025.
6. Meyers, A.I.; Reider, P. Stereoselective synthesis of threo-3-hydroxy-2-methylcarbocylic acids using alkoxyalkyl propionates. J. Chem. Soc. 1979, 101, 2501.
7. Cheng, Z.-Y.; Bin, L.; Long, Q.-H. A modified procedure for the deprotection of methoxymethyl ether. Tetrahedron Letter 2000, 41, 819-822.
8. Monti, H.; Leandri, G.; Klos-Rinquet, M.; Corriol, C. An efficient deprotective method for allylic alcohols protected as methoxyethoxymethyl (MEM) and methoxymethyl ether. Synth. Commun. 1983, 13, 1021.
9. Ireland, R.E.; Vamey, M.D.J. Approach to the total synthesis of chlorothricolide: synthesis of (+-)-19,20-dihydro-24-O-methylchlorothricolide methyl ester ethyl carbonate. J. Org. Chem. 1986, 51, 635.
10. Quindon, Y.; Morton, H.E.; Yoalim, C. Dimethylboron bromide and diphenylboron bromide. Acetal and ketal cleavage. Cleavage of MEM, MOM and MTM ethers. Tetrahedron Lett. 1983, 24, 3969.
11. Shibasaki, M.; Ishida, Y.; Okabe, N. A novel synthesis of (-)-carpetimycin. Tetrahedron Lett. 1985, 26, 2217.
12. Corey, E.J.; Hua, D.H.; Seitz, S.P. Methods for the interconversion of protective groups. Transformation of MEM ethers into isopropylthiomethyl ethers or cyanomethyl ethers. Tetrahedron Lett. 1984, 25, 3.
13. Boeckman, R.k., Jr.; Potenza, J.C. Catechol boron halides: mild and selective reagents for cleavage of common protecting groups. Tetrahedron Lett. 1985, 26, 1411.
14. Stephen, H.; Daniel, D.; Yves, D. Mild cleavage of methoxymethyl (MOM) ethers with trimethylsilyl bromide. Tetrahedron Lett. 1984, 25, 2515.
15. Lee, A.S.-Y.; Hu, Y.-J.; Chu, S.-F. A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers. Tetrahedron 2001, 57, 2121-2126.