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

Year: 2024

Type: article

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.

Source: ChemistrySelect

DOI: 10.1002/slct.202404952

Authors: Doddegowdana Ramegowda Adarsh, Thadakamalla Ravi Teja, Allam Vinaykumar, B. Sridhar, B. V. Subba Reddy

Institutions: Indian Institute of Chemical Technology, Academy of Scientific and Innovative Research

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India

OpenAlex ID: W4404320771

FWCI: 0.278

Cites: 16

Cited by: 2

Related to: 10