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Synthesis of Carboxy ATTO 647N Using Redox Cycling for Xanthone Access.

ABSTRACT: A synthesis of the carbopyronine dye Carboxy ATTO 647N from simple materials is reported. This route proceeds in 11 forward steps from 3-bromoaniline with the key xanthone intermediate formed using a new oxidation methodology. The step utilizes an oxidation cycle with base, water, iodine, and more than doubles the yield of the standard permanganate oxidation methodology, accessing gram-scale quantities of this late-stage product. From this, Carboxy ATTO 647N was prepared in only four additional steps. This facile route to a complex fluorophore is expected to enable further studies in fluorescence imaging.

SUBMITTER: Bachman JL

PROVIDER: S-EPMC7549415 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Carboxy ATTO 647N Using Redox Cycling for Xanthone Access.

Bachman James L JL Pavlich Cyprian I CI Boley Alexander J AJ Marcotte Edward M EM Anslyn Eric V EV

Organic letters 20191211 2

A synthesis of the carbopyronine dye Carboxy ATTO 647N from simple materials is reported. This route proceeds in 11 forward steps from 3-bromoaniline with the key xanthone intermediate formed using a new oxidation methodology. The step utilizes an oxidation cycle with base, water, iodine, and more than doubles the yield of the standard permanganate oxidation methodology, accessing gram-scale quantities of this late-stage product. From this, Carboxy ATTO 647N was prepared in only four additional ...[more]

PMID: 31825225

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