Synthesis of penta- N-protected thermopentamine and its selective deprotection

The synthesis of the penta- N-protected polyamine thermopentamine {PA 3433, 1a, tert-butyl N-[13-allyl-16-( N′-phthalimido)-9-(pyridine-2-sulfonyl)-4-trimethylsilylethanesulfonyl-4,9,13-triazahexadec-1-yl]carbamate};, containing five independently removable N-protecting groups is described. These pr...

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Bibliographic Details
Published in:Tetrahedron 1998-07, Vol.54 (28), p.8035-8046
Main Authors: Kyoung Pak, Jae, Guggisberg, Armin, Hesse, Manfred
Format: Article
Language:English
Subjects:
Alkaloids
Polyamines
Protecting groups
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Summary:The synthesis of the penta- N-protected polyamine thermopentamine {PA 3433, 1a, tert-butyl N-[13-allyl-16-( N′-phthalimido)-9-(pyridine-2-sulfonyl)-4-trimethylsilylethanesulfonyl-4,9,13-triazahexadec-1-yl]carbamate};, containing five independently removable N-protecting groups is described. These protecting groups include tert-butoxycarbonyl, trimethylsilylethanesulfonyl, pyridine-2-sulfonyl, allyl and phthalimido replaced with a trifluoroacetyl group for the deprotection of pyridine-2-sulfonyl group. The selective deprotection of each functional group has been investigated. The synthesis of the penta- N-protected polyamines thermopentamines {PA 3433, 1a and 1b}, containing five independently removable N-protecting groups is described. The selective deprotection of each functional group has been investigated.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00442-6