120316-53-2

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 563-63-3 silver(I) acetate 
• 120408-91-5 3-O-(tert-butyldimethylsilyl)-6-deoxy-D-glucal 

Downstream Products

• 120316-55-4 Acetic acid (2R,3S,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester 
• 192653-61-5 C₄₅H₇₄O₄SeSi 
• 120316-58-7 C₄₅H₆₂O₁₁Se₂Si 
• 120316-61-2 (2R,3R,4S,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-phenylselanyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 1. Stereochemistry of the reactions of D-glucal derivatives with phenylsulfenyl chloride and phenylselenenyl chloride

The stereoselectivity of the reactions of D-glucal derivatives with PhSCl and PhSeCl is dependent on the presence of an electronegative heteroatom substituent at C(6) and the nature of the functionality at C(4). The C(6)-substituent influences the conformational preferences of the D- glucal derivatives, and greatest stereoselectivity is obtained with those glycals that preferentially exist in the inverted 5H4 half-chair conformation 28b. A polar substituent at C(4) increases the selectivity by stabilizing the episulfonium/episelenonium ion intermediates 31b and 33.

SELENIUM-MEDIATED GLYCOSIDATIONS: A SELECTIVE SYNTHESIS OF β-2-DEOXYGLYCOSIDES

1,2-Trans diequatorial acetoxy-selenides are selectively prepared from glycals.Their activation by trimethylsilyl trifluoromethanesulfonate in the presence of sugar alcohols followed by reductive deselenation leads to an efficient access to Β-2-deoxyglyco