440122-32-7

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 82598-90-1 ethyl 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)acetate 
• 82659-59-4 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 

Downstream Products

• 440122-31-6 (S)-Phenylselanyl-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 
• 440122-33-8 (R)-Phenylselanyl-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 

Relevant academic research and scientific papers

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.