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SOME INTRAMOLECULAR REARRANGEMENTS WHEN PENTOFURANOSES ARE TREATED WITH DIETHYLAMINOSULFUR TRIFLUORIDE (DAST)
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UNSPECIFIED (1993) SOME INTRAMOLECULAR REARRANGEMENTS WHEN PENTOFURANOSES ARE TREATED WITH DIETHYLAMINOSULFUR TRIFLUORIDE (DAST). JOURNAL OF FLUORINE CHEMISTRY, 60 (2-3). pp. 239-250. ISSN 0022-1139.
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Abstract
Treatment of methyl 2,3-O-isopropylidene-beta-D-ribofuranoside with DAST gave a good yield of 2,3-O-isopropylidene-5-0-methyl-beta-D-ribofuranosyl fluoride in which the methoxy group had migrated from C-1 --> C-5 and been replaced with retention of configuration by fluorine. The corresponding aldehyde when treated under similar conditions underwent a similar migration to give 5-deoxy-5-fluoro-2,3-O-isopropylidene-5-O-methyl-beta-D-ribofuranosyl fluoride. A similar migration occurred with methyl 2',3'-di-O-acetyl-beta-D-ribofuranoside and with acetyl 2,3-O-isopropylidene-D-ribofuranose but not with 1,2,3-tri-O-acetyl-D-ribofuranose. Thus the migration depends upon the migratory aptitude of the substituent at C-1 and the conformation of the furanose ring. Two ribofuranosyl fluorides were used as starting materials from which to make nucleosides by the method of Noyori and Hayoshi.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF FLUORINE CHEMISTRY | ||||
Publisher: | ELSEVIER SCIENCE SA LAUSANNE | ||||
ISSN: | 0022-1139 | ||||
Official Date: | February 1993 | ||||
Dates: |
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Volume: | 60 | ||||
Number: | 2-3 | ||||
Number of Pages: | 12 | ||||
Page Range: | pp. 239-250 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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