Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone
Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is simi...
| Main Authors: | , , , , , , , , |
|---|---|
| Formato: | Journal article |
| Idioma: | English |
| Publicado em: |
2008
|
| _version_ | 1826286959510683648 |
|---|---|
| author | Booth, K da Cruz, F Hotchkiss, D Jenkinson, S Jones, N Weymouth-Wilson, A Clarkson, R Heinz, T Fleet, G |
| author_facet | Booth, K da Cruz, F Hotchkiss, D Jenkinson, S Jones, N Weymouth-Wilson, A Clarkson, R Heinz, T Fleet, G |
| author_sort | Booth, K |
| collection | OXFORD |
| description | Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone. © 2008 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T01:51:27Z |
| format | Journal article |
| id | oxford-uuid:9a3c3d1c-d54e-4e2e-aea5-5cbe5f7eff45 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:51:27Z |
| publishDate | 2008 |
| record_format | dspace |
| spelling | oxford-uuid:9a3c3d1c-d54e-4e2e-aea5-5cbe5f7eff452022-03-27T00:19:53ZCarbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactoneJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9a3c3d1c-d54e-4e2e-aea5-5cbe5f7eff45EnglishSymplectic Elements at Oxford2008Booth, Kda Cruz, FHotchkiss, DJenkinson, SJones, NWeymouth-Wilson, AClarkson, RHeinz, TFleet, GReadily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25%; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60% yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone. © 2008 Elsevier Ltd. All rights reserved. |
| spellingShingle | Booth, K da Cruz, F Hotchkiss, D Jenkinson, S Jones, N Weymouth-Wilson, A Clarkson, R Heinz, T Fleet, G Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone |
| title | Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone |
| title_full | Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone |
| title_fullStr | Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone |
| title_full_unstemmed | Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone |
| title_short | Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C-methyl-ribono-1,4-lactone and 2-C-methyl-arabinonolactone |
| title_sort | carbon branched carbohydrate chirons practical access to both enantiomers of 2 c methyl ribono 1 4 lactone and 2 c methyl arabinonolactone |
| work_keys_str_mv | AT boothk carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT dacruzf carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT hotchkissd carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT jenkinsons carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT jonesn carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT weymouthwilsona carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT clarksonr carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT heinzt carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone AT fleetg carbonbranchedcarbohydratechironspracticalaccesstobothenantiomersof2cmethylribono14lactoneand2cmethylarabinonolactone |