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Open-chain acetonides of D-galactono-1,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids

Abstract:

Treatment of D-gaIactono-l,4-lactone with dimethoxypropane in acetone in the presence of tosic acid forms methyl 2,3:5,6-di-0-isopropylidene-D-galactonate 6 (with only the secondary hydroxy group at C-4 unprotected) and methyl 2,3:4,5-di-O-isopropyIidene-D-galactonate 5 (with only the primary hydroxy group at C-6 unprotected) in yields of 20% and 78%, respectively. The value of such easily accessible intermediates is illustrated by the synthesis of l,4-dideoxy-l,4-imino-D-glucitol 16 (a pyrro...

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Publication status:
Published

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Publisher copy:
10.1039/a809807g

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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
8
Pages:
901-908
Publication date:
1999-04-21
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:b0e60b4e-4325-4e07-aa00-e13c892ecb2e
Source identifiers:
37009
Local pid:
pubs:37009
Language:
English

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