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10.1021/acs.joc.0c02986

http://scihub22266oqcxt.onion/10.1021/acs.joc.0c02986
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33733767!ä!33733767

suck abstract from ncbi


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pmid33733767      J+Org+Chem 2021 ; 86 (7): 5065-5072
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  • Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate #MMPMID33733767
  • Xie Y; Hu T; Zhang Y; Wei D; Zheng W; Zhu F; Tian G; Aisa HA; Shen J
  • J Org Chem 2021[Apr]; 86 (7): 5065-5072 PMID33733767show ga
  • Currently, remdesivir is the first and only FDA-approved antiviral drug for COVID-19 treatment. Adequate supplies of remdesivir are highly warranted to cope with this global public health crisis. Herein, we report a Weinreb amide approach for preparing the key intermediate of remdesivir in the glycosylation step where overaddition side reactions are eliminated. Starting from 2,3,5-tri-O-benzyl-d-ribonolactone, the preferred route consisting of three sequential steps (Weinreb amidation, O-TMS protection, and Grignard addition) enables a high-yield (65%) synthesis of this intermediate at a kilogram scale. In particular, the undesirable PhMgCl used in previous methods was successfully replaced by MeMgBr. This approach proved to be suitable for the scalable production of the key remdesivir intermediate.
  • |Adenosine Monophosphate/*analogs & derivatives/chemical synthesis[MESH]
  • |Alanine/*analogs & derivatives/chemical synthesis[MESH]
  • |Amides/*chemistry[MESH]


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