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An Expeditious Total Synthesis of 5'-Deoxy-toyocamycin and 5'-Deoxysangivamycin.

ABSTRACT: In present paper, an expeditious total synthesis of naturally occurring 5'-deoxytoyocamycin and 5'-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-?-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra.

SUBMITTER: Dong X

PROVIDER: S-EPMC6413189 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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An Expeditious Total Synthesis of 5'-Deoxy-toyocamycin and 5'-Deoxysangivamycin.

Dong Xiangyou X Tang Jie J Hu Chen C Bai Jiang J Ding Haixin H Xiao Qiang Q

Molecules (Basel, Switzerland) 20190219 4

In present paper, an expeditious total synthesis of naturally occurring 5'-deoxytoyocamycin and 5'-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved interm ...[more]

PMID: 30791372

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