D-glucosamine propanedithioacetal, an efficient chiral auxiliary in beta-lactam chemistry.
The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C3, C4, and C1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity.
Anaya
J
J
Departamento de Química Orgánica, Universidad de Salamanca, Spain. janay@gugu.usal.es
Gero
S D
SD
Grande
M
M
Hernando
J I
JI
Laso
N M
NM
D000818:Animals; D002850:Chromatography, Gel; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D006801:Humans; D007962:Leukocytes / Q000201:enzymology; D008956:Models, Chemical; D010179:Pancreas / Q000201:enzymology; D010196:Pancreatic Elastase / Q000378:metabolism; D051381:Rats; D047090:beta-Lactams / Q000138:chemical synthesis*
D047090:beta-Lactams; C121492:glucosamine propanedithioacetal; D010196:Pancreatic Elastase; D005944:Glucosamine