title: Reduction of sugar lactones to hemiacetals with lithium triethylborohydride.
abstract: Reduction of ribono-1,4-lactones and gulono-1,4-lactone as well as ribono-1,5-lactone and glucono-1,5-lactones with LTBH (1.2 equiv.) in CH2Cl2 at 0 °C for 30 min provided the corresponding pentose or hexose hemiacetals in high yields. Commonly used in carbohydrate chemistry protecting groups such as trityl, benzyl, silyl, acetals and to some extent acyls are compatible with this reduction.
authors.affiliation: Department of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
authors.forename: Cesar
authors.initials: C
authors.lastname: Gonzalez
authors.affiliation: Department of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
authors.forename: Sam
authors.initials: S
authors.lastname: Kavoosi
authors.affiliation: Department of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
authors.forename: Andersson
authors.initials: A
authors.lastname: Sanchez
authors.affiliation: Department of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA. Electronic address: wnuk@fiu.edu.
authors.forename: Stanislaw F
authors.initials: SF
authors.lastname: Wnuk
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry; D005942:Gluconates / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000080:Acetals; D001894:Borohydrides; D005942:Gluconates; D007783:Lactones; C057020:ribonolactone; D012266:Ribose; D008094:Lithium; C010730:beta-glucono-1,5-lactone
keywords: Hemiacetals; Lithium triethylborohydride; Reduction; Sugar lactols; Sugar lactones; Super-hydride