A concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivatives

The chemical synthesis of 1,2,4-tri- O-acetyl-3-deoxy-3-fluoro-5-thio- d-xylopyranose, 1,2,4,6-tetra- O-acetyl-3-deoxy-3-fluoro-5-thio-α- d-glucopyranose and their corresponding nucleosides of thymine is described. Treatment of 3-fluoro-5- S-acetyl-5-thio- d-xylofuranose, obtained by hydrolysis of t...

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Published in:Carbohydrate research 2008-05, Vol.343 (6), p.1099-1103
Main Authors: Tsoukala, Evangelia, Manta, Stella, Tzioumaki, Niki, Agelis, George, Komiotis, Dimitri
Format: Article
Language:English
Subjects:
3-Fluoro-5-thio-glucopyranose
3-Fluoro-5-thioxylopyranose
Molecular Structure
Pyrans - chemistry
Thionucleosides
Thiosugars
Thiosugars - chemical synthesis
Thymidine - analogs & derivatives
Thymidine - chemical synthesis
Thymidine - chemistry
Thymine
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cited_by cdi_FETCH-LOGICAL-c360t-709a2c973b457597754d278c2f459ff5a90931e593a07fafb259e6969b23f043
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container_end_page 1103
container_issue 6
container_start_page 1099
container_title Carbohydrate research
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creator Tsoukala, Evangelia
Manta, Stella
Tzioumaki, Niki
Agelis, George
Komiotis, Dimitri
description The chemical synthesis of 1,2,4-tri- O-acetyl-3-deoxy-3-fluoro-5-thio- d-xylopyranose, 1,2,4,6-tetra- O-acetyl-3-deoxy-3-fluoro-5-thio-α- d-glucopyranose and their corresponding nucleosides of thymine is described. Treatment of 3-fluoro-5- S-acetyl-5-thio- d-xylofuranose, obtained by hydrolysis of the isopropylidene group of 3-fluoro-1,2- O-isopropylidene-5- S-acetyl-5-thio- d-xylofuranose, with methanolic ammonia and direct acetylation, led to triacetylated 3-deoxy-3-fluoro-5-thio- d-xylopyranose. Condensation of acetylated 3-fluoro-5-thio- d-xylopyranose with silylated thymine afforded the corresponding nucleoside. Selective benzoylation and direct methanesulfonylation of 3-fluoro-1,2- O-isopropylidene-α- d-glucofuranose gave the 6- O-benzoyl-5- O-methylsulfonyl derivative, which on treatment with sodium methoxide afforded the 5,6-anhydro derivative. Treatment of the latter with thiourea, followed by acetolysis, gave the 3-fluoro-5- S-acetyl-6- O-acetyl-1,2- O-isopropylidene-5-thio-α- d-glucofuranose. 3-Fluoro-5- S-acetyl-6- O-acetyl-5-thio- d-glucofuranose, obtained after hydrolysis of 5-thiofuranose isopropylidene, was treated with ammonia in methanol and directly acetylated, giving tetraacetylated 3-deoxy-3-fluoro-5-thio-α- d-glucopyranose. Condensation of the latter with silylated thymine afforded the desired 3-deoxy-3-fluoro-5-thio-β- d-glucopyranonucleoside analogue.
doi_str_mv 10.1016/j.carres.2008.02.004
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Treatment of 3-fluoro-5- S-acetyl-5-thio- d-xylofuranose, obtained by hydrolysis of the isopropylidene group of 3-fluoro-1,2- O-isopropylidene-5- S-acetyl-5-thio- d-xylofuranose, with methanolic ammonia and direct acetylation, led to triacetylated 3-deoxy-3-fluoro-5-thio- d-xylopyranose. Condensation of acetylated 3-fluoro-5-thio- d-xylopyranose with silylated thymine afforded the corresponding nucleoside. Selective benzoylation and direct methanesulfonylation of 3-fluoro-1,2- O-isopropylidene-α- d-glucofuranose gave the 6- O-benzoyl-5- O-methylsulfonyl derivative, which on treatment with sodium methoxide afforded the 5,6-anhydro derivative. Treatment of the latter with thiourea, followed by acetolysis, gave the 3-fluoro-5- S-acetyl-6- O-acetyl-1,2- O-isopropylidene-5-thio-α- d-glucofuranose. 3-Fluoro-5- S-acetyl-6- O-acetyl-5-thio- d-glucofuranose, obtained after hydrolysis of 5-thiofuranose isopropylidene, was treated with ammonia in methanol and directly acetylated, giving tetraacetylated 3-deoxy-3-fluoro-5-thio-α- d-glucopyranose. 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Treatment of 3-fluoro-5- S-acetyl-5-thio- d-xylofuranose, obtained by hydrolysis of the isopropylidene group of 3-fluoro-1,2- O-isopropylidene-5- S-acetyl-5-thio- d-xylofuranose, with methanolic ammonia and direct acetylation, led to triacetylated 3-deoxy-3-fluoro-5-thio- d-xylopyranose. Condensation of acetylated 3-fluoro-5-thio- d-xylopyranose with silylated thymine afforded the corresponding nucleoside. Selective benzoylation and direct methanesulfonylation of 3-fluoro-1,2- O-isopropylidene-α- d-glucofuranose gave the 6- O-benzoyl-5- O-methylsulfonyl derivative, which on treatment with sodium methoxide afforded the 5,6-anhydro derivative. 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Treatment of 3-fluoro-5- S-acetyl-5-thio- d-xylofuranose, obtained by hydrolysis of the isopropylidene group of 3-fluoro-1,2- O-isopropylidene-5- S-acetyl-5-thio- d-xylofuranose, with methanolic ammonia and direct acetylation, led to triacetylated 3-deoxy-3-fluoro-5-thio- d-xylopyranose. Condensation of acetylated 3-fluoro-5-thio- d-xylopyranose with silylated thymine afforded the corresponding nucleoside. Selective benzoylation and direct methanesulfonylation of 3-fluoro-1,2- O-isopropylidene-α- d-glucofuranose gave the 6- O-benzoyl-5- O-methylsulfonyl derivative, which on treatment with sodium methoxide afforded the 5,6-anhydro derivative. Treatment of the latter with thiourea, followed by acetolysis, gave the 3-fluoro-5- S-acetyl-6- O-acetyl-1,2- O-isopropylidene-5-thio-α- d-glucofuranose. 3-Fluoro-5- S-acetyl-6- O-acetyl-5-thio- d-glucofuranose, obtained after hydrolysis of 5-thiofuranose isopropylidene, was treated with ammonia in methanol and directly acetylated, giving tetraacetylated 3-deoxy-3-fluoro-5-thio-α- d-glucopyranose. Condensation of the latter with silylated thymine afforded the desired 3-deoxy-3-fluoro-5-thio-β- d-glucopyranonucleoside analogue.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>18313037</pmid><doi>10.1016/j.carres.2008.02.004</doi><tpages>5</tpages></addata></record>
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subjects 3-Fluoro-5-thio-glucopyranose
3-Fluoro-5-thioxylopyranose
Molecular Structure
Pyrans - chemistry
Thionucleosides
Thiosugars
Thiosugars - chemical synthesis
Thymidine - analogs & derivatives
Thymidine - chemical synthesis
Thymidine - chemistry
Thymine
title A concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivatives
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