77734-07-7

Upstream product

• 77733-97-2 2-Butyl-4,5-dihydro-1,3-dioxepin 
• 77734-07-7 2-Butyltetrahydro-3-furancarbaldehyd 
• 61732-95-4 2-n-butyl-4,7-dihydro-1,3-dioxepine 

Downstream Products

• 77734-07-7 (2α,3β)-(+/-)-2-Butyltetrahydro-3-furancarbaldehyd 
• 77734-07-7 (2α,3α)-(+/-)-2-Butyltetrahydro-3-furancarbaldehyd 
• 99488-06-9 (2α,3α)-(+/-)-2-Butyltetrahydro-3-(tosyloxymethyl)furan 
• 89163-43-9 cis-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 
• 87433-77-0 trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 

Relevant academic research and scientific papers

Diastereoselective Synthesis of cis- or trans-2,3-Substituted Tetrahydrofurans and 3,4-Substituted 4-Butanolides

Improved synthesis of 10 and the epimerisation 10 --> 11 yield cis- and trans-tetrahydro-3-furancarbaldehydes (10,11) with high diastereoselectivity. 10 as well as 11 are reduced by the Wolff-Kishner procedure to give 2-substituted 3-methyltetrahydrofurans 15 with trans configuration. 2-Substituted 3-methyltetrahydrofurans with cis configuration 14 are synthesized via 10 --> 12 --> 13 --> 14.The furans 14 and 15 possess structural features of naturally occurring 4-butanolides like quercus lactone a, quercus lactone b, or eldanolide which is the pheromone of the sugarcane borer Eldana saccharina (Wlk.). 14 and 15 are readily oxidized with CrO3/Ac2O to yield the lactones 16 and 17, whereas oxidation with Ru oxides proved to be less effective.The synthesis of rac-1 and rac-2 is described.

Stereoselective synthesis of tetrahydrofuran-3-carbaldehyde

Trans-tetrahydrofuran-3-carbaldehydes are prepared by ruthenium-catalyzed isomerization of 4,7-dihydro-1,3-dioxepines and subsequent Lewis acid-catalyzed 1,3-alkyl migration.