149299-69-4

Upstream product

• 100-39-0 benzyl bromide 
• 149299-67-2 methyl 2,6-anhydro-3-O-tert-butyldiphenylsilyl-2-thio-α-D-mannopyranoside 
• 28642-64-0 methyl 4,6-O-benzylidene-2-O-benzoyl-α-D-glucopyranoside 
• 149404-15-9 methyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 149299-65-0 methyl 2-S-acetyl-4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-thio-α-D-mannopyranoside 
• 149299-66-1 methyl-2-S-acetyl-4-O-benzoyl-6-bromo-6-deoxy-3-O-tert-butyldiphenylsilyl-2-thio-α-D-mannopyranoside 
• 149299-63-8 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 149299-64-9 methyl 4,6-O-benzylidene-3-O-tert-butyldiphenylsilyl-2-O-trifluoromethanesulfonyl-α-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 149299-70-7 methyl 2,6-anhydro-4-O-benzyl-2-thio-α-D-mannopyranoside 
• 149299-74-1 (2R,3S,4R,5S)-3,4-dibenzyloxy-5-hydroxy-2-hydroxymethylthiane 
• 149299-71-8 methyl 2,6-anhydro-3,4-di-O-benzyl-2-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Enantiospecific synthesis of 1-deoxythiomannojirimycin from a derivative of D-glucose

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.