Substrate Directed Highly Diastereoselective Synthesis of Eliglustat: A Drug for Gaucher Disease

Abstract A highly diastereoselective total synthesis of Eliglustat has been accomplished starting from a readily available D‐serine. This novel route involves a four‐step telescoped process to afford the keto intermediate ( 4 ) in 74% overall yield. The diastereoselective reduction of 4 using sodium borohydride provides the alcohol, a key intermediate 5 , with excellent selectivity (>99 dr) and yield (95%). The total synthesis of Eliglustat from D‐serine has been accomplished in ten steps with an overall yield of 21%. This process not only gives a desirable yield but also avoids the use of hazardous conditions.

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Journal
ChemistrySelect
Published
2024-11-01
DOI
https://doi.org/10.1002/slct.202404952
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Substrate Directed Highly Diastereoselective Synthesis of Eliglustat: A Drug for Gaucher Disease

D.R. Adarsh, B. V. Subba Reddy, Allam Vinaykumar, Balasubramanian Sridhar et al.
ChemistrySelect
Carbohydrate Chemistry and Synthesis
article

Substrate Directed Highly Diastereoselective Synthesis of Eliglustat: A Drug for Gaucher Disease

D.R. Adarsh, B. V. Subba Reddy, Allam Vinaykumar, Balasubramanian Sridhar, T. Ravi Teja
article en

Abstract

Abstract A highly diastereoselective total synthesis of Eliglustat has been accomplished starting from a readily available D‐serine. This novel route involves a four‐step telescoped process to afford the keto intermediate ( 4 ) in 74% overall yield. The diastereoselective reduction of 4 using sodium borohydride provides the alcohol, a key intermediate 5 , with excellent selectivity (>99 dr) and yield (95%). The total synthesis of Eliglustat from D‐serine has been accomplished in ten steps with an overall yield of 21%. This process not only gives a desirable yield but also avoids the use of hazardous conditions.

ChemistrySelectVol. 9(43)
Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India
Good health and well-being
Openalex Percentile: Top 85%
Carbohydrate Chemistry and Synthesis
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