13312-25-9

Upstream product

• 138768-42-0 (+/-)-4-<1,3-Dihydro-4-(tert-butyldimethylsilyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl>-3-hydroxy-2-methylbutene 
• 64-17-5 ethanol 
• 24280-93-1 mycophenolic acid 
• 138768-41-9 2-(4-((tert-butyldimethylsilyl)oxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde 
• 193277-88-2 4-Hydroxy-2-methoxy-5-methyl-3,6-dihydro-2H-benzo[2,1-b;3,4-c']difuran-8-one 
• 24953-96-6 (4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde 
• 78-39-7 Triethyl orthoacetate 
• 138768-43-1 Ethyl E-6-<1,3-Dihydro-4-(tert-butyldimethylsilyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl>-4-methyl-4-hexenoate 
• 193277-85-9 6-(2-hydroxy-3-methylbut-3-enyl)-5-methoxy-7-(2-methoxyethoxymethoxy)-4-methyl-3H-isobenzofuran-2-one 
• 172151-14-3 [6-methoxy-4-(2-methoxyethoxymethoxy)-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl]-acetaldehyde 
• 193277-77-9 2,4-Dimethoxy-5-methyl-3,6-dihydro-2H-benzo[2,1-b;3,4-c']difuran-8-one 

Downstream Products

• 24280-93-1 mycophenolic acid 

Relevant academic research and scientific papers

Total synthesis of mycophenolic acid

A total synthesis of mycophenolic acid is reported. Diels-Alder reaction of [5-methoxy-3-(1-methoxypropenyl)-4,5-dihydrofuran-2-yloxy]-trimethylsilane with 3-benzenesulfinyl-5H-furan-2-one afforded the hexasubstituted nucleus. The side chain was constructed from the unveiled aldehyde. A total synthesis of mycophenolic acid is reported. Diels-Alder reaction of [5-methoxy-3-(1-methoxypropenyl)-4, 5-dihydrofuran-2-yloxy]-trimethylsilane with 3-benzenesulfinyl-5H-furan-2-one afforded the hexasubstituted nucleus. The side chain was constructed from the unveiled aldehyde.

The Orthoester Claisen Rearrangement in the Synthesis of Mycophenolic Acid

The orthoester Claisen rearrangement is used as a key reaction in the facile conversion of an acetaldehyde moiety stereospecifically into the (E)-4-methylhex-4-enoic acid side-chain of mycophenolic acid.

Phosphamide derivative as well as preparation method and application thereof

The invention relates to a compound of a general formula (I), a stereoisomer or pharmaceutically acceptable salt of the compound and application of the compound in preparation of medicines for preventing or treating diabetes, resisting tumors, preventing or treating attention deficit hyperactivity disorder and motor neuron diseases, protecting brain and preventing or treating central nervous system related diseases, immunosuppression, organ tissue or cell allogeneic suppression rejection reaction, immune regulation and/or inflammatory diseases, convulsions, epilepsy or cerebral apoplexy. The structure of the compound of the general formula (I) is Q-L-R, and the groups of the compound are defined in the specification.

The synthesis of mycophenolic acid

A new synthesis of mycophenolic acid 1, has been accomplished using silyloxy-1,3-cyclohexadiene 9 which undergoes cycloaddition to dimethyl acetylenedicarboxylate and subsequent elimination of ethylene (Alder-Rickert reaction) to give the trisubstituted dimethyl phthalate 11. After conversion of 11 to phthalide 16, the (E)-4-methyl-4-hexenoic acid side-chain was constructed via an orthoester Claisen rearrangement using allylic alcohol 19 and triethyl orthoacetate.