256390-79-1

Upstream product

• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 625-45-6 2-methoxyacetic acid 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 493021-16-2 (2R,3S,4R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(octadecane-1-sulfonyl)-tetrahydro-pyran 
• 493021-17-3 (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(octadecane-1-sulfonyl)-tetrahydro-pyran 
• 256390-60-0 (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(octadecane-1-sulfonyl)-tetrahydro-pyran 
• 256390-61-1 (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-octadec-(Z)-ylidene-tetrahydro-pyran 
• 256390-59-7 C₄₅H₆₆O₄S 

Relevant academic research and scientific papers

Anomeric effects of sulfones

The anomeric effect of the sulfone group in tetrahydropyrans has been determined. The value is >2 kcal mol-1, which is larger than the A-value of a methyl group but less than the A-value of the sulfone in a tetrahydropyran. Hence, in an unsubstituted tetrahydropyranyl sulfone, the equatorial conformer predominates, whereas in a properly substituted methyltetrahydropyranyl sulfone, an axial sulfone is preferred over an axial methyl group.

Convergent C-glycolipid synthesis via the Ramberg-Baecklund reaction: active antiproliferative glycolipids.

[formula: see text] A novel methodology has been developed, employing the Ramberg-Baecklund rearrangement and ionic hydrogenation to synthesize C-glycosides with high stereoselectivity at the anomeric center. The C-glycolipid 14b exhibits antiproliferativ