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1.
Org Biomol Chem ; 18(26): 5017-5033, 2020 07 08.
Article in English | MEDLINE | ID: mdl-32573638

ABSTRACT

We developed an indirect synthetic method for α-l-fucosides. Based on the fact that l-fucose is 6-deoxy-l-galactose, our strategy consists of the stereoselective construction of α-l-galactoside and its conversion to α-l-fucoside via C6-deoxygenation. The formation of α-l-galactoside is strongly directed using 4,6-O-di-tert-butylsilylene(DTBS)-protected l-galactosyl donors. The DTBS-directed α-l-galactosylation showed broad substrate applicability along with excellent coupling yield and α-selectivity. In the C6-deoxygenation of α-l-galactosides, the Barton-McCombie reaction facilitated the conversion to l-fucosides with good yield. To demonstrate the applicability of our method, we synthesized naturally occurring α-l-fucosides.


Subject(s)
Fucose/chemical synthesis , Galactosides/chemistry , Oxygen/chemistry , Carbohydrate Conformation , Fucose/chemistry , Glycosylation , Stereoisomerism
2.
RSC Adv ; 9(48): 28241-28247, 2019 Sep 03.
Article in English | MEDLINE | ID: mdl-35530445

ABSTRACT

A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthesis. The target compound shows enzyme activity in the presence of α-galactosidase.

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