Enantioselective and protecting group-free synthesis of 1-deoxythionojirimycin, 1-deoxythiomannojirimycin, and 1-deoxythiotalonojirimycin.
1-Deoxythioglyconojirimycins were synthesized by using a protecting group-free strategy, starting from readily available carbohydrates, in good overall yield. Use of benzyltriethylammonium tetrathiomolybdate, [BnEt(3)N](2)MoS(4), as a sulfur transfer reagent and borohydride exchange resin (BER) reduction of a lactone enabled the efficient synthesis of the title compounds.
Gunasundari
Thanikachalam
T
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Chandrasekaran
Srinivasan
S
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
C554656:1-deoxythionojirimycin; D002241:Carbohydrates; D017485:1-Deoxynojirimycin