Continuous-Flow Synthesis of (R)-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir

被引：16
作者：
Suveges, Nicolas S. [1 ]
Rodriguez, Anderson A. [1 ]
Diederichs, Carla C. [1 ]
de Souza, Stefania P. [1 ]
Leao, Raquel A. C. [1 ,2 ]
Miranda, Leandro S. M. [1 ]
Horta, Bruno A. C. [3 ]
Pedraza, Sergio F. [4 ]
de Carvalho, Otavio V. [4 ]
Pais, Karla C. [4 ]
Terra, Jose H. C. [4 ]
de Souza, Rodrigo O. M. A. [1 ,2 ]
机构：
[1] Univ Fed Rio de Janeiro, Chem Inst, Biocatalysis & Organ Synth Grp, BR-21941909 Rio De Janeiro, Brazil
[2] Univ Fed Rio de Janeiro, Sch Pharm, Rio De Janeiro, Brazil
[3] Univ Fed Rio de Janeiro, Chem Inst, BR-21941909 Rio De Janeiro, Brazil
[4] Nortec Quim SA, Dist Ind Duque Caxias Xerem, BR-25250612 Rio De Janeiro, Brazil
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 23期
关键词：
Continuous flow; Flow chemistry; Kinetic resolution; Chirality; Domino reactions; Synthesis design; RESOLUTION; CHEMISTRY; MOIETY; GREEN;
D O I：
10.1002/ejoc.201800345
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(R)-Propylene carbonate is an important intermediate in the synthesis of tenofovir pro-drugs such as tenofovir alafenamide fumarate (TAF) and tenofovir diisoproyl fumarate (TDF). Independent of the pro-drug type, tenofovir presents a chiral secondary hydroxy derivative, which can be obtained directly from (R)-propylene carbonate. Herein, we report our chemo-enzymatic continuous-flow strategy towards (R)-propylene carbonate starting from a very cheap and renewable raw material, glycerol. We were able to synthesize (R)-propylene carbonate in seven continuous-flow steps, starting from glycerol, in good-to-excellent yields (66-93%) and excellent selectivity (E > 200).
引用
收藏
页码：2931 / 2938
页数：8
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