Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose
The sequential reactions of 2-C-methyl-d-arabinose with cyanamide and methyl propiolate afford an anhydronucleoside, which may be opened under acid conditions with inversion at C2′, to give 2′-C-methyl uridine; ring opening with sodium hydroxide gave 2′-C-methyl arabino-uridine with retention of con...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2007
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| _version_ | 1797095296786759680 |
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| author | Jenkinson, S Jones, N Moussa, A Stewart, A Heinz, T Fleet, G |
| author_facet | Jenkinson, S Jones, N Moussa, A Stewart, A Heinz, T Fleet, G |
| author_sort | Jenkinson, S |
| collection | OXFORD |
| description | The sequential reactions of 2-C-methyl-d-arabinose with cyanamide and methyl propiolate afford an anhydronucleoside, which may be opened under acid conditions with inversion at C2′, to give 2′-C-methyl uridine; ring opening with sodium hydroxide gave 2′-C-methyl arabino-uridine with retention of configuration at C2′. This gives complete stereospecific control to yield only β-nucleosides. © 2007 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T04:25:51Z |
| format | Journal article |
| id | oxford-uuid:cc97270c-676b-4fac-aa84-083d88e853fc |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:25:51Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:cc97270c-676b-4fac-aa84-083d88e853fc2022-03-27T07:23:04ZAnomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinoseJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:cc97270c-676b-4fac-aa84-083d88e853fcEnglishSymplectic Elements at Oxford2007Jenkinson, SJones, NMoussa, AStewart, AHeinz, TFleet, GThe sequential reactions of 2-C-methyl-d-arabinose with cyanamide and methyl propiolate afford an anhydronucleoside, which may be opened under acid conditions with inversion at C2′, to give 2′-C-methyl uridine; ring opening with sodium hydroxide gave 2′-C-methyl arabino-uridine with retention of configuration at C2′. This gives complete stereospecific control to yield only β-nucleosides. © 2007 Elsevier Ltd. All rights reserved. |
| spellingShingle | Jenkinson, S Jones, N Moussa, A Stewart, A Heinz, T Fleet, G Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose |
| title | Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose |
| title_full | Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose |
| title_fullStr | Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose |
| title_full_unstemmed | Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose |
| title_short | Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose |
| title_sort | anomeric stereospecific synthesis of 2 c methyl beta nucleosides the holy reaction of cyanamide with 2 c methyl d arabinose |
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