57432-86-7

Upstream product

• 59067-07-1 3-bromopropinaldehyde diethyl acetal 
• 13133-62-5 thiophenolate 
• 108-98-5 thiophenol 
• 27098-65-3 3-phenylsulfanyl-propionaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 149-73-5 trimethyl orthoformate 
• 35573-93-4 3-chloro-1,1-diethoxy-propane 

Downstream Products

• 57398-27-3 (3,3-diethoxy-propane-1-sulfonyl)-benzene 
• 94298-99-4 2-(2-phenylsulfanyl-ethyl)-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 86531-03-5 3-(phenylthio)-2-methylenepropan-1-al 
• 124389-40-8 4-ethoxy-6-phenylthio-1-hexene 
• 86531-35-3 (Z)-1-(β-methoxyethoxy)-3-<(phenylthio)methyl>-1,3-butadiene 
• 86531-07-9 (E)-1-(β-methoxyethoxy)-3-<(phenylthio)methyl>-1,3-butadiene 
• 54815-13-3 pelargonaldehyde diethyl acetal 
• 53305-11-6 1,1-diethoxy-4-methyl-pentane 
• 53356-85-7 (4,4-diethoxybutyl)benzene 
• 57398-47-7 3-Benzenesulfonyl-4-methyl-pentanal 
• 57398-46-6 3-Benzenesulfonyl-4-phenyl-butyraldehyde 
• 57398-45-5 3-Benzenesulfonyl-nonanal 
• 57398-33-1 (1,1-Diethoxy-4-methyl-pentane-3-sulfonyl)-benzene 
• 57398-39-7 (1,1-Diethoxy-3,4-dimethyl-pentane-3-sulfonyl)-benzene 

Relevant academic research and scientific papers

Baker's yeast mediated biohydrogenation of sulphur-functionalised methacrolein derivatives. Stereochemical aspects of the reaction and preparation of the two enantiomers of useful C4 bifunctional chiral synthons

The baker's yeast mediated reduction of sulphur-functionalised methacroleins 11, 15 and 18 leads to the preparation of the bifunctional methyl branched C4 chiral synthons 6 and 7. The stereochemical aspects of the biohydrogenation have been investigated. Both the oxidation state of sulphur and the isomeric position of the double bond affected the enantioselectivity of the reduction strongly, thus, offering access to the two enantiomeric forms of 6 and 7.

Allylation Using Allylborates

A study has been carried out on the scope of allylation of a range of acetals activated by trimethylsilyl trifluoromethanesulfonate (TMSOTf) using a number of organoborates.Intermolecular allylation of acyclic acetals proceeds smoothly and in high yield using lithium n-butyltriallylborate or lithium methyltriallylborate in THF at -78 deg C while 1,3-dioxanes and dioxolanes give rise to some reduction products.Intramolecular allylation may be carried out via anchoring the triallylborane using an alkoxide anion.Mechanistic studies indicate that allyl transfer is from boron and not silicon, while stereoselectivity studies on the crotylation of acyclic acetals as well as the allylation of chiral acetals derived from (2R,4R)-pentanediol indicate moderate levels of diastereoselection.

SYNTHESIS OF FUNCTIONALIZED ISOPRENES INVOLVING A TERMINAL ALKOXY GROUP AND THEIR HIGHLY REGIOSELECTIVE DIELS-ALDER REACTION

Functionalized isoprenes involving a terminal alkoxy group are newly synthesized, and a highly regioselective Diels-Alder reaction of these dienes with various unsymmetric dienophiles is described.