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
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 hydrox...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
1999
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| _version_ | 1826291532404097024 |
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| author | Long, D Stetz, R Nash, R Marquess, D Lloyd, J Winters, A Asano, N Fleet, G |
| author_facet | Long, D Stetz, R Nash, R Marquess, D Lloyd, J Winters, A Asano, N Fleet, G |
| author_sort | Long, D |
| collection | OXFORD |
| description | 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 pyrrolidine), and for the efficient preparation of 6-azido-6-deoxy-D-galactono1,4-lactone 22. The conversion of 22 to a seven-rhembered galactonolactam 21 (a tetrahydroxycaprolactam) may provide access to hydroxylated nylon polymers. The galactonolactam 21 has no significant inhibitory effect on a number of glycosidases. Reaction of 22 with triflic anhydride gives two epimeric 5-(azidomethyl)tetrahydrofuran-2carboxylates which provide starting materials for two series of carbopeptoids, one of which probably has a helical structure and the other a structure reminiscent of a β-turn. |
| first_indexed | 2024-03-07T03:00:48Z |
| format | Journal article |
| id | oxford-uuid:b0e60b4e-4325-4e07-aa00-e13c892ecb2e |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:00:48Z |
| publishDate | 1999 |
| record_format | dspace |
| spelling | oxford-uuid:b0e60b4e-4325-4e07-aa00-e13c892ecb2e2022-03-27T03:59:50ZOpen-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 carbopeptoidsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b0e60b4e-4325-4e07-aa00-e13c892ecb2eEnglishSymplectic Elements at Oxford1999Long, DStetz, RNash, RMarquess, DLloyd, JWinters, AAsano, NFleet, GTreatment 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 pyrrolidine), and for the efficient preparation of 6-azido-6-deoxy-D-galactono1,4-lactone 22. The conversion of 22 to a seven-rhembered galactonolactam 21 (a tetrahydroxycaprolactam) may provide access to hydroxylated nylon polymers. The galactonolactam 21 has no significant inhibitory effect on a number of glycosidases. Reaction of 22 with triflic anhydride gives two epimeric 5-(azidomethyl)tetrahydrofuran-2carboxylates which provide starting materials for two series of carbopeptoids, one of which probably has a helical structure and the other a structure reminiscent of a β-turn. |
| spellingShingle | Long, D Stetz, R Nash, R Marquess, D Lloyd, J Winters, A Asano, N Fleet, G 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
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