120633-57-0

Upstream product

• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 128766-41-6 Toluene-4-sulfonic acid (S)-2,2-dimethyl-4-((Z)-3-phenyl-but-2-enyl)-[1,3]dioxolan-4-ylmethyl ester 
• 111649-99-1 (3S)-3,4-O-isopropylidene-3,4-dihydroxy-3-p-toluenesulfonyloxymethyl-butanal 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 212763-45-6 (-)-(2R)-2-hydroxy-2-(hydroxymethyl)-2,2'-O-isopropylidenepent-4-enol 
• 128766-40-5 Toluene-4-sulfonic acid (S)-2,2-dimethyl-4-(3-oxo-butyl)-[1,3]dioxolan-4-ylmethyl ester 
• 128766-39-2 4-((R)-4-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 111649-98-0 (2S)-1,2-O-isopropylidene-2-p-toluenesulfonyloxymethyl-pent-4-ene-1,2-diol 

Downstream Products

• 111650-02-3 (1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane 
• 120633-58-1 (6S)-6,7-O-isopropylidene-6,7-dihydroxy-6-p-toluenesulfonyloxymethyl-hepta-2-one 

Relevant academic research and scientific papers

C-H insertion method for the chiral tertiary alcohol: Formal synthesis of (-)-frontalin

Intramolecular insertion of the alkylidene carbene into C - H bond adjacent to the protected secondary hydroxyl group gave a chiral tertiary alcohol derivative, which was converted to a synthetic intermediate 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