Straightforward stereoselective synthesis of 1-thio-β-d-mannosides and 1-thio-β-l-rhamnosides. (24th March 2023)

• Record Type: Journal Article
• Authors: Shit, Pradip; Kundu, Monalisa; Kumar Misra, Anup
• Is Part Of: Tetrahedron letters. Volume 118(2023)
• Publication Date: 2023-03-24
• Subjects: Thioglycoside -- Glycoside -- d-Mannose -- d-Rhamnose -- Stereoselective -- Sulfur; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2023.154391
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: An efficient direct synthesis of β-d -mannosides and β-l -rhamnosides have been achieved in very good yield by the treatment of per- O -acetyl-α-d -mannopyranosyl bromide and per- O -acetyl-α-l -rhamnopyranosyl bromide respectively with a combination of sodium sulfide nonahydrate (Na2 S⋅9H2 O) and carbon disulfide (CS2 ) and subsequent treatment of the anomeric β-thiols with carbohydrate derived electrophiles. The high nucleophilicity and slow anomerization of the intermediate anomeric β-thiol derivatives provides the target β-thioglycosides in simple and practical manner.