111650-02-3

Upstream product

• 204325-80-4 Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester 
• 24400-75-7 ethylene-cetal de la bromo-5 pentanone-2 
• 98-59-9 p-toluenesulfonyl chloride 
• 111649-99-1 (3S)-3,4-O-isopropylidene-3,4-dihydroxy-3-p-toluenesulfonyloxymethyl-butanal 
• 111649-98-0 (2S)-1,2-O-isopropylidene-2-p-toluenesulfonyloxymethyl-pent-4-ene-1,2-diol 
• 212763-45-6 (-)-(2R)-2-hydroxy-2-(hydroxymethyl)-2,2'-O-isopropylidenepent-4-enol 
• 120633-57-0 (6S)-6,7-O-isopropylidene-6,7-dihydroxy-6-p-toluenesulfonyloxymethyl-hept-3-ene-(E)-2-one 
• 204325-75-7 (3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran 
• 204325-79-1 ((R)-Toluene-4-sulfinyl)-acetic acid (S)-2-benzyloxy-6-oxo-2-(toluene-4-sulfonyloxymethyl)-heptyl ester 
• 204325-78-0 ((R)-Toluene-4-sulfinyl)-acetic acid (E)-(S)-2-benzyloxy-6-oxo-2-(toluene-4-sulfonyloxymethyl)-hept-4-enyl ester 
• 204589-34-4 (R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol 
• 204325-72-4 5-Benzyloxy-6-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 204325-77-9 ((R)-Toluene-4-sulfinyl)-acetic acid (S)-2-benzyloxy-4-oxo-2-(toluene-4-sulfonyloxymethyl)-butyl ester 
• 204325-76-8 Toluene-4-sulfonic acid (S)-3-benzyloxy-6-((R)-toluene-4-sulfinylmethyl)-3,4-dihydro-2H-pyran-3-ylmethyl ester 

Relevant academic research and scientific papers

Chemoenzymatic enantioselective synthesis of (1S,5R)-(-)-frontalin

The pheromone (1S,5R)-(-)-frontalin was synthesized in 90% e.e. via a chemoenzymatic route. The key step was the stereoselective acylation (desymmetrization) of 2-(4,5-dihydroxy-4-hydroxymethylpentyl)-2-methyl-1,3-dioxolane with vinyl acetate in organic m

1,6-Asymmetric induction utilizing Asymmetric desymmetrization by diastereoselective C-O bond fission of the 4-substituted bicyclic acetal: Application to a synthesis of (-)-frontalin

1,6-Asymmetric induction was achieved in the acid-induced diastereoselective acetal cleavage reaction of a 4-substituted bicyclic acetal 8 bearing a chiral sulfinyl group. On treatment with titanium tetrachloride and 2,6-disubstituted pyridine bases, 8 gave a synthetically versatile 3,3-disubstituted dihydropyran derivative 9a with moderate diastereoselectivity. The utility of this chiral synthon was successfully demonstrated by a formal synthesis of (-)-frontalin.

TOTAL SYNTHESIS OF (S)-(-) AND (R)-(+)-FRONTALIN AND OF (-)-MALYNGOLIDE FROM THE BRANCHED-CHAIN SUGAR "α"-D-ISOSACCHARINO-LACTONE AS CHIRAL TEMPLATE

Highly enantiomerically pure (S)-(-) 2 and (R)-(+)-frontalin 3 and (-)-malyngolide 4 were synthesized from the common chiral building block, (2R)-1,2-O-isopropylidene-2-hydroxymethyl-pent-4-ene-1,2-diol 9 readily prepared in five steps and 35percent overa