1,2:5,6-Di-O-isopropylidene-3-O-methanesulfonyl-a-D-glucofuranose - CAS 5450-26-0
Category:
Carbohydrates
Product Name:
1,2:5,6-Di-O-isopropylidene-3-O-methanesulfonyl-a-D-glucofuranose
CAS Number:
5450-26-0
Molecular Weight:
338.37
Molecular Formula:
C13H22O8S
COA:
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MSDS:
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Structure:
Monosaccharides
Chemical Structure
CAS 5450-26-0 1,2:5,6-Di-O-isopropylidene-3-O-methanesulfonyl-a-D-glucofuranose

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Reference Reading


1.A concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivatives.
Tsoukala E1, Manta S, Tzioumaki N, Agelis G, Komiotis D. Carbohydr Res. 2008 May 5;343(6):1099-103. doi: 10.1016/j.carres.2008.02.004. Epub 2008 Feb 10.
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-alpha-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-alpha-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-alpha-D-glucofuranose.