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METHYL 5-O-TERT-BUTYLDIPHENYLSILYL-2-DEOXY-D-THREO-PENTOFURANOSIDE - AN APPROACH TO THE SYNTHESIS OF 3'-SUBSTITUTED-2',3'-DIDEOXYNUCLEOSIDES INCLUDING 3'-AZIDO-3'-DEOXYTHYMIDINE AND OF 3'-SUBSTITUTED-2',3'-DIDEOXY-C-NUCLEOSIDES

Abstract:

The Barton deoxygenation of methyl 3,5-O-isopropylidene-αβ-D-xylofuranoside is the key step in a short synthesis of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-αβ-D-threo-pentofuranoside (1) from D-xylose. The syntheses of methyl 2,3-dideoxy-3-fluoro-gaβ-D-erythro-pentofuranoside and of a protected 3-azido-2,3-dideoxy-D-erythro-pentofuranose, a possible intermediate for the synthesis of 3′-azido-3'-deoxythymidine (AZT), are reported and the potential of (1) as a divergent intermediate for the ...

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Publication status:
Published

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Journal:
TETRAHEDRON LETTERS
Volume:
28
Issue:
31
Pages:
3615-3618
Publication date:
1987-01-01
DOI:
ISSN:
0040-4039
URN:
uuid:9030ad34-bce5-4be3-a96f-20ccf5f1a944
Source identifiers:
42716
Local pid:
pubs:42716
Language:
English

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