A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE
Deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol] may be prepared in moderate amounts in an overall yield of 35% in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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1989
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| _version_ | 1826259643229274112 |
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| author | Fleet, G Ramsden, N Witty, D |
| author_facet | Fleet, G Ramsden, N Witty, D |
| author_sort | Fleet, G |
| collection | OXFORD |
| description | Deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol] may be prepared in moderate amounts in an overall yield of 35% in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar. A synthesis of (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is reported. © 1989. |
| first_indexed | 2024-03-06T18:53:06Z |
| format | Journal article |
| id | oxford-uuid:10ea5d17-f665-449b-b717-85dade14c129 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:53:06Z |
| publishDate | 1989 |
| record_format | dspace |
| spelling | oxford-uuid:10ea5d17-f665-449b-b717-85dade14c1292022-03-26T09:59:04ZA PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSEJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:10ea5d17-f665-449b-b717-85dade14c129EnglishSymplectic Elements at Oxford1989Fleet, GRamsden, NWitty, DDeoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol] may be prepared in moderate amounts in an overall yield of 35% in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar. A synthesis of (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is reported. © 1989. |
| spellingShingle | Fleet, G Ramsden, N Witty, D A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE |
| title | A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE |
| title_full | A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE |
| title_fullStr | A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE |
| title_full_unstemmed | A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE |
| title_short | A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE |
| title_sort | practical synthesis of deoxymannojirimycin and of 2s 3r 4r 5r 3 4 5 trihydroxypipecolic acid from d glucose |
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