191285-50-4

Upstream product

• 142-61-0 Hexanoyl chloride 
• 25018-68-2 2,3-O-isopropylidene-β-D-threo-2-pentulofuranose 
• 87-72-9 D-Xylose 
• 66696-79-5 5-(1-hydroxyhexylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 191285-49-1 ((3aS,6R,6aS)-6-Benzyloxy-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-3a-yl)-methanol 

Relevant academic research and scientific papers

Concise Syntheses of (-)- and (+)-Syringolide 1 and (-)-Δ7-Syringolide 1

(-)- and (+)-Syringolide 1 have been synthesized from 2,3-O-isopropylidene-β-threo-pentulofuranose (1), which was readily prepared from D- or L-xylose, respectively. Condensation of 1 with 3-oxooctanoic acid and treatment of the ester with TFA:H2O (9:1) produced syringolide 1 in 6.3% yield for the two steps. According to the same synthetic route by replacing 3-oxooctanoic acid with 3-oxo-7-octenoic acid, (-)-Δ7-syringolide 1 was prepared in 5.8% yield. Primary β-keto esters of arabinulose and fructose were also prepared to test the selectivity of the biomimetic cyclization to form syringolide analogs.