A new synthesis of 3′‐deoxy‐3′‐fluoroadenosine, a key intermediate of cyclic dinucleotide

Author:

Qiu Yayun1,Li Zixing1,Ning Fangmin1,Tang Dandan1,Chen Huansheng12ORCID

Affiliation:

1. School of Pharmacy Xiamen Medical College Xiamen P.R. China

2. Xiamen Key Laboratory of Traditional Chinese Medicine Bioengineering Xiamen P.R. China

Abstract

AbstractA new synthesis of 3′‐deoxy‐3′‐fluoroadenosine for use as an important intermediate of antitumor‐active cyclic dinucleotide is disclosed. The synthesis started with the known 5‐O‐TBDPS‐D‐lyxofuranose 1,2‐acetonides, which was first transformed into a fluorinated compound after the DAST reaction. Desilylation and acidic methanolysis were then finished in one pot. After a sequence of triflation, displacement by OBz as well as benzoylation, perbenzoylated 3‐deoxy‐3‐fluoro‐D‐ribofuranoside was obtained, which would be transformed to 3′‐deoxy‐3′‐fluoroadenosine as the key intermediate of cyclic dinucleotide after ammonolysis.

Publisher

Wiley

Subject

Organic Chemistry

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