Preliminary studies on the transformation of nitrosugars into branched chain iminosugars: synthesis of 1,4-dideoxy-4-C-hydroxymethyl-1,4-imino-pentanols.
A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehyde followed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-known glycosidase inhibitor 1,4-dideoxy-1,4-imino-pentanol. This strategy also afforded a new route to some other interesting derivatives, such as N-hydroxy, N-propyloxy, and imino derivatives, a new kind of compounds with promising biological properties. [reaction: see text].
Otero
José M
JM
Departamento de Química OrgAnica, Universidade de Santiago, 15782 Santiago de Compostela, Spain.
Soengas
Raquel G
RG
Estévez
Juan C
JC
Estévez
Ramón J
RJ
Watkin
David J
DJ
Evinson
Emma L
EL
Nash
Robert J
RJ
Fleet
George W J
GW
D000478:Alkylation; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005557:Formaldehyde; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D008958:Models, Molecular; D009574:Nitro Compounds / Q000138:chemical synthesis*; D000439:Pentanols / Q000138:chemical synthesis* / Q000494:pharmacology*; D011759:Pyrrolidines / Q000138:chemical synthesis; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D050111:Imino Sugars; D007202:Indicators and Reagents; D009574:Nitro Compounds; D000439:Pentanols; D011759:Pyrrolidines; D005557:Formaldehyde; D006026:Glycoside Hydrolases