Synthesis 2020; 52(03): 417-423
DOI: 10.1055/s-0039-1690732
paper
© Georg Thieme Verlag Stuttgart · New York

Practical Synthesis of Fludarabine and Nelarabine

Chunyang Shen
,
Jiang Liu
,
Wenliang Ouyang
,
Haixin Ding
,
Jiang Bai
,
Qiang Xiao
The project was supported by the National Natural Science Foundation of China (NO. 21676131, 21462019,), the Jiangxi Provincial Department of Science and Technology (No. 20143ACB20012), the Education Department of Jiangxi Province (No. 170673) and the Jiangxi­ Science & Technology Normal University (Doctor Startup Fund 2018BSQD022).
Further Information

Publication History

Received: 09 September 2019

Accepted after revision: 07 October 2019

Publication Date:
30 October 2019 (online)

Abstract

A new practical synthesis strategy has been developed to access­ the β-d-arabinofuranosyl purine nucleosides fludarabine and nelarabine. In our approach, an ortho-alkyne benzoyl ester is transiently introduced as a neighbouring-participation group in Vorbrüggen glycosylation to afford the corresponding β-nucleoside exclusively. The latter was further removed efficiently by using freshly prepared Ph3PAuOTFA to give the corresponding 2′-OH nucleosides without transesterification. After reversion of the configuration of 2′-OH and deprotection, fludarabine and nelarabine were obtained in high yield and purity.

Supporting Information

 
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