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Synthesis of some N-substituted methyl 2,3-dideoxy-2,3-epimino-?-D-lyxofuranosides

✍ Scribed by Cleophax, J.; Gero, S. D.; Hildesheim, J.; Sepulchre, A. M.; Guthrie, R. D.; Smith, C. W.

Book ID
121408025
Publisher
The Royal Society of Chemistry
Year
1970
Tongue
English
Weight
902 KB
Volume
0
Category
Article
ISSN
0022-4952

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Synthesis of a 2,3-dideoxy-2,3-difluorof
Synthesis of a 2,3-dideoxy-2,3-difluorofuranose with the d-lyxo configuration. An intramolecular rearrangement of methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-d-lyxofuranoside observed during the attempted synthesis of 1-(2,3-dideoxy-2,3-difluoro-β-d-lyxofuranosyl)thymine
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A new sugar, methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-D-lyxofuranoside (8), which features fluorine substituents on adjacent carbon positions above the plane of the tetrahydrofuran ring, was synthesized from 1,2: 5,6-di-O-isopropylidine-alpha-D-allofuranose in seven steps and 22% overall yield. D