Improved synthesis of the Kijanimicin oligodeoxytetrasaccharide

• Published in: Carbohydrate research Vol. 471; pp. 19 - 27
• Main Authors: Thiem, Joachim, Sajus, Henry
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.01.2019; Elsevier
• Subjects: 2,6-Dideoxy sugars; Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Life Sciences & Biomedicine; Oligodeoxy-oligosaccharides; Physical Sciences; S-hexopyranosyl phosphorodithioates; Science & Technology; Stereoselective α- and β-glycosylations; Oligodeoxy-oligosaccharides; 2,6-Dideoxy sugars; S-hexopyranosyl phosphorodithioates; Stereoselective α- and β-glycosylations; Stereoselective alpha- and beta-glycosylations; ABSOLUTE STEREOCHEMISTRY; DERIVATIVES; SUGAR
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2018.10.014

By sequential synthesis the four 2,6-dideoxy saccharide moieties of the kijanimicin tetrasaccharide could be stereoselectively assembled. For formation of all required 2-deoxy α-glycoside linkages various S-(hexopyranosyl)-phosphorodithioates as donor structures could be convincingly employed. The terminal 2-deoxy β-glycoside linkage was stereoselectively formed following the dibromomethyl methyl ether approach. The target octadeoxy-tetrasaccha-ride could be obtained via nine subsequent steps in 5% overall yield. [Display omitted] •Stereoselective synthesis of oligodeoxy-oligosaccharides.•Glycosylations employing S-hexopyranosyl phosphorodithioates.•Use of DBE reaction for formation of β-linked 2,6-dideoxy-glycosides.