Synthesis of rare L-altro sugars and C6-Derivatives

A divergent synthesis to rare L-altro sugars and C-6 derivatives from easily available d-galactose is described. The important intermediate, L-altro epoxide 28, was provided by regioselective protections, regioselective 6-O-benzoylation/5-O-mesylation, and intramolecular SN2 inversion at C-5 as key...

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Bibliographic Details
Published in:Tetrahedron 2023-08, Vol.143, p.133555, Article 133555
Main Authors: Ting, Yen-Ju, Yang, Ya-Han, Ho, Guo-Ming, Hung, Shang-Cheng
Format: Article
Language:English
Subjects:
6-Deoxy- l-altrose
6-Deoxy- l-hexose
Carbohydrate chemistry
l-Altrose
l-Hexose
Rare sugars
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Summary:A divergent synthesis to rare L-altro sugars and C-6 derivatives from easily available d-galactose is described. The important intermediate, L-altro epoxide 28, was provided by regioselective protections, regioselective 6-O-benzoylation/5-O-mesylation, and intramolecular SN2 inversion at C-5 as key steps. The following nucleophilic addition on the epoxide ring with H−, CN−, and N3− afforded the corresponding 6-deoxy-, 6-cyano-, and 6-azido-L-altrofuranosides, respectively. Hydrolysis of the epoxide 28 under acidic conditions furnished the 1,6-anhydro-L-altro sugar 38, which could undergo sequential thioglycosylation and oxidation to yield l-altrose-derived thioglycoside 40. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133555