Carbohydrate Research p. 109 - 118 (1993)
Update date:2022-08-02
Topics:
Cubero
Lopez-Espinosa
Richardson
Suarez Ortega
1-Deoxythiomannojirimycin [2, (2R,3S,4R,5S)-3,4,5-trihydroxy-2-hydroxymethylthiane], a thio analogue of the glycosidase inhibitor 1-deoxymannojirimycin [1, (2R,3S,4R,5S)-3,4,5-trihydroxy-2-hydroxymethylpiperidine], has been synthesised from methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside. The key reactions involved inversion of configuration at C-2 with the introduction of a thio function and cyclisation to give methyl 2,6-anhydro-2-thio-α-D-mannopyranoside (12). Hydrolysis of the 3,4-di-O-benzyl derivative (15) of 12 and reduction of the product with borohydride gave (2R,3S,4R,5S)-3,4-dibenzyloxy-5-hydroxy-2-hydroxymethylthiane (18). Hydrogenolysis of 18 yielded 2, which was a weak competitive inhibitor of yeast α-D-glucosidase but was inactive against almond β-D-glucosidase. 1-Deoxythiomannojirimycin [2, (2R,3S,4R,5S)-3,4,5-trihydroxy-2-hydroxymethylthiane], a thio analogue of the glycosidase inhibitor 1-deoxymannojirimycin [1, (2R,3S,4R,5S)-3,4,5-trihydroxy-2-hydroxymethylpiperidine], has been synthesised from methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside. The key reactions involved inversion of configuration at C-2 with the introduction of a thio function and cyclisation to give methyl 2,6-anhydro-2-thio-α-D-mannopyranoside (12). Hydrolysis of the 3,4-di-O-benzyl derivative (15) of 12 and reduction of the product with borohydride gave (2R,3S,4R,5S),-3,4-dibenzyloxy-5-hydroxy-2-hydroxymethylthiane (18). Hydrogenolysis of 18 yielded 2. which was a weak competitive inhibitor of yeast α-D-glucosidase but was inactive against almond β-D-glucosidase.
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