118533-11-2

Upstream product

• 2916-76-9 methyl (trimethylsilyl)acetate 
• 65247-32-7 benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside 
• 5927-18-4 trimethyl phosphonoacetate 
• 100-51-6 benzyl alcohol 
• 245729-74-2 benzyl 3,4-O-isopropylidene arabinoside 
• 250224-22-7 (3R,4S,5S)-2-Benzyloxy-tetrahydro-pyran-3,4,5-triol 
• 87-72-9 L-(+)-arabinose 
• 28070-06-6 (3aS,7aS)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one 
• 96-32-2 bromoacetic acid methyl ester 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 7473-38-3 benzyl β-L-arabinopyranoside 

Downstream Products

• 118533-12-3 (4RS, 7S, 7aR)-4,7-dihydroxy-7,7a-dihydrofuro<3,2-c>pyran-2(4H, 6H)-one 
• 118533-10-1 (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one 
• 135195-42-5 (R)-O-benzylpatulin 

Relevant academic research and scientific papers

Ylidenebutenolide Mycotoxins. Concise Syntheses of Patulin and Neopatulin from Carbohydrate Precursors

Conversion of arabinose 10 to the protected ketone 13 followed by Wittig condensation to 14, acidcatalysed cyclisation (to lactone 16), dehydration and deprotection provides a brief synthesis of the mycotoxic substance patulin 1, which is produced by Penicillium and Aspergillus spp.In a similar manner, the biogenetic precursor to patulin, neopatulin 8, is synthesized from lyxose 25 via the key intermediates 24, 28 and 30.

A CONCISE SYNTHESIS OF PATULIN FROM ARABINOSE

Conversion of arabinose (5) to the protected ketone (7), followed by Wittig condensation to (9), acid catalysed cyclisation (to 10), and dehydration, provides a brief synthesis of the fungal metabolite patulin (1), produced by Penicillium and Aspergilius