Synthesis of 1-Deoxymannojirimycin from d-Fructose using the Mitsunobu Reaction.
J Org Chem
; 87(24): 16895-16901, 2022 12 16.
Article
em En
| MEDLINE
| ID: mdl-36460300
ABSTRACT
Three different Mitsunobu reactions have been investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ) from d-fructose. The highest yielding and most practical synthesis can be undertaken on a 10 g scale with minimal chromatography. In the key step, N,O-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-α-d-fructofuranose under Mitsunobu conditions to give 14. Acidic hydrolysis affords nitrone 15, which reduces quantitatively via catalytic hydrogenolysis to afford 1-DMJ (4) in 55% overall yield from d-fructose (cf. 37% for azide route and 29% for nosyl route).
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
1-Desoxinojirimicina
/
Frutose
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article