Short and general procedure for synthesizing cis-1,2-fused 1,3-oxathiolan-, 1,3-oxaselenolan-, and 1,3-oxazolidin-2-imine carbohydrate derivatives.
Novel cis-1,2-fused 1,3-oxathiolan-, 1,3-oxaselenolan-, and 1,3-oxazolidin-2-imine carbohydrate derivatives have been prepared by treatment of the corresponding 1,2-anhydrosugars with potassium thiocyanate, potassium selenocyanate, and sodium cyanamide, respectively. The procedure is compatible with several protecting groups such as acyl, benzyl, and silyl and also with sugars of different configurations.
Castilla
Javier
J
Departament de Química Analitica i Química Orgànica, Universitat Rovira i Virgili, 43007 Tarragona, Spain.
Marín
Irene
I
Matheu
M Isabel
MI
Díaz
Yolanda
Y
Castillón
Sergio
S
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
C548187:1,3-oxazolidin-2-imine; D002241:Carbohydrates; D007097:Imines; D010080:Oxazoles; D018036:Selenium Compounds; D013876:Thiophenes; C013177:1,3-oxathiolane