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Synthesis of the C8'-epimeric thymine pyranosyl amino acid core of amipurimycin.

ABSTRACT: The C8'-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to the formation of the pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 12. Functional group manipulation in 12 gave 21 that on stereoselective ?-glycosylation afforded the pyranosyl thymine nucleoside 2 - a core of amipurimycin.

SUBMITTER: Markad PR

PROVIDER: S-EPMC4979907 | biostudies-other | 2016

REPOSITORIES: biostudies-other

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Synthesis of the C8'-epimeric thymine pyranosyl amino acid core of amipurimycin.

Markad Pramod R PR Kumbhar Navanath N Dhavale Dilip D DD

Beilstein journal of organic chemistry 20160805

The C8'-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to the formation of the pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 12. Functional group manipu ...[more]

PMID: 27559421

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