Hydrogen fluoride-mediated synthesis of 1-thiotrehaloses involving reaction of D-glucose with hydrogen sulfide.
Hydrogen sulfide reacted with D-glucose in hydrogen fluoride solution to yield preponderantly alpha,alpha-1-thiotrehalose, beta,beta-1-thiotrehalose, and the alpha,beta anomer. Conditions were found under which the thiotrehaloses were obtained in the respective proportions of 8:5:5.
Defaye
J
J
Département de Recherche Fondamentale, C.N.R.S., Centre d'Etudes Nucléaires, Grenoble, France.
Gadelle
A
A
Pedersen
C
C
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005947:Glucose; D006858:Hydrofluoric Acid; D006862:Hydrogen Sulfide; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D013438:Sulfhydryl Compounds; D014199:Trehalose; D005947:Glucose; D006858:Hydrofluoric Acid; D006862:Hydrogen Sulfide