499121-75-4

Upstream product

• 499121-72-1 (2S,3S,5S)-5-Allyl-2-(2-hydroxy-ethyl)-tetrahydro-furan-3-ol 
• 499121-73-2 (3aS,5S,6aS)-5-Allyl-tetrahydro-furo[3,2-b]furan-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 499121-74-3 (2S,3S,5S)-5-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-3-ol 

Downstream Products

• 499121-76-5 Acetic acid 3-{(2S,4S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-propyl ester 
• 499121-78-7 Acetic acid 3-{(2S,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-oxo-tetrahydro-furan-2-yl}-propyl ester 
• 499121-77-6 3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propan-1-ol 
• 474005-66-8 3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde 

Relevant academic research and scientific papers

A practical synthesis of the F-ring of halichondrin B via ozonolytic desymmetrization of a C2-symmetric dihydroxycyclohexene

C2-symmetric dihydroxycyclohexene 1 was desymmetrized via a one-pot Criegee ozonolysis/acylation protocol to afford acetal-lactone 2. Installation of the allyl side chain on the convex face of the bicyclic system and subsequent reduction provided the desired tetrahydrofuran 4 with the correct relative and absolute stereochemistries. Simple functional group manipulations led to the desired F-ring module 3 of halichondrin B.