A practical approach to Dideoxy-1, 4- and 1, 5-iminopentitols from protected sugar hemiacetals. (1st December 2019)

• Record Type: Journal Article
• Authors: Jaszczyk, Justyna; Li, Sizhe; Cocaud, Chloé; Nicolas, Cyril; Martin, Olivier R.
• Is Part Of: Carbohydrate research. Volume 486(2019)
• Publication Date: 2019-12-01
• Subjects: Sugar hemiacetals -- N-tert-butanesulfinyl glycosylamines -- Aminoalditols -- Dideoxyiminopentitols; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2019.107855
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: The convenient and straightforward preparation of dideoxy-1, 4- and 1, 5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert -butanesulfinyl glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest. Graphical abstract: Image 1 Highlights: Short, general and convenient method. Synthesis of dideoxy-1, 4- and 1, 5-iminopentitols from protected sugar hemiacetals. Use of a sulfinyl glycosylamine as an aldose imine equivalent. Moderate to good overall yields (24–55%) obtained through two reaction sequences of 2.5 and 3.5 h.