389121-73-7

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 6921-34-2 benzylmagnesium chloride 
• 1428331-87-6 C₄₁H₄₀O₅ 
• 591-50-4 iodobenzene 
• 1428331-88-7 C₃₅H₃₆O₅ 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 872706-01-9 (2R,3R,4S,5R,6R)-2-acetoxy-2-benzyl-3,4,5-tris(benzyloxy)-6-(benzyloxy)methyltetrahydropyran 
• 155590-31-1 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane 
• 216869-51-1 (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(phenyl)methylidene-D-glucopyranose 

Relevant academic research and scientific papers

A new oxa-Michael reaction and a gold-catalysed cyclisation en route to C-glycosides

Two new syntheses of benzyl C-glycosides have been developed. The first one involves an unprecedented oxa-Michael cyclisation and the second one relies on an efficient gold-catalysed ring-closure.

Stereochemistry in the synthesis and reaction of exo-glycals.

Two general methods are explored for the stereoselective synthesis of exo-glycals. One method utilizes a nucleophilic addition of fully protected sugar lactones of gluco-, galacto-, and manno-types, followed by the subsequent dehydration, to give the desired exo-glycals with (Z)-configuration. The other method proceeds with selenylation of C-glycosides in a stereoselective manner. The subsequent selenoxide elimination also provides (Z)-exo-glycals. The prepared exo-glycal conjugated esters of either gluco- or manno-type react with allyl alcohol to give exclusively alpha-anomers.

Facile synthesis of conjugated exo-glycals

Two efficient methods were explored for the synthesis of various conjugated exo-glycals: (i) by nucleophilic addition of sugar lactones with a subsequent dehydration, and (ii) by selenylation of C-glycosides with subsequent selenoxide elimination. These reactions occurred in a stereoselective manner to give exclusively or predominantly the (Z)-isomers of exo-glycals.