Flow chemistry based catalytic hydrogenation for improving the synthesis of 1-deoxynojirimycin (DNJ) from an l-sorbose derived precursor.
Carbohydr Res
; 529: 108845, 2023 Jul.
Article
em En
| MEDLINE
| ID: mdl-37210941
ABSTRACT
1-Deoxynojirimycin (1-DNJ) is a glycoprocessing inhibitor, and it serves as a synthetic precursor to two of three currently marketed iminosugar drugs, miglustat (N-butyl DNJ/Zavesca®) and miglitol (Glyset®). Herein a continuous flow procedure is presented that shortens a synthesis of 1-DNJ from an intermediate prepared from l-sorbose. Batch reactions involving an azide reduction, subsequent reductive amination-based cyclisation, and O-benzyl deprotection in a previous report required two steps and the use of an acid. Here, this sequence is achieved in one step using the H-Cube® MiniPlus continuous flow reactor. Subsequent reductive amination of 1-DNJ with butanal using the H-Cube® gave NB-DNJ.
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Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Sorbose
/
1-Desoxinojirimicina
Idioma:
En
Ano de publicação:
2023
Tipo de documento:
Article