64584-93-6

Upstream product

• 108-22-5 Isopropenyl acetate 
• 111957-98-3 Pent-4-en-2-ol 
• 108-05-4 vinyl acetate 

Downstream Products

• 1393927-28-0 (2R,4S)-4-{[(tert-butyl)diphenylsilyl]oxy}-5-hydroxypentan-2-yl acetate 
• 1393927-26-8 (2R,4S,5S)-4-{[(tert-Butyl)diphenylsilyl]oxy}-5-hydroxyhept-6-en-2-yl acetate 
• 1393927-37-1 C₂₅H₃₄O₄Si 
• 1393927-36-0 (2R,4S)-4-{[(tert-butyl)diphenylsilyl]oxy}-4-[(2S)-2,5-dihydro-5-oxo-furan-2-yl]butan-2-yl acetate 
• 1393927-35-9 (3S,4S,6R)-6-(acetyloxy)-4-{[(tert-butyl)diphenylsilyl]oxy}hept-1-en-3-yl acrylate 
• 1393927-33-7 (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate 
• 869336-49-2 (-)-(2R,4S,4'R)-6-(4'-acetoxypentyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 
• 869336-56-1 (+)-(2R,4R,4'R)-6-(4'-acetoxypentyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 
• 879282-80-1 (R)-5-{(1S,3R,5R,6S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-triisopropylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]hept-1-yl}-pentan-2-ol 
• 869336-63-0 (-)-(2R,4S,4'R)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 
• 869336-70-9 (+)-(2R,4R,4'R)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 

Relevant academic research and scientific papers

Synthesis and glycosidase inhibition studies of 5-methyl-substituted tetrahydroxyindolizidines and -pyrrolizidines related to natural hyacinthacines B

The synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B and their biological evaluation as glycosidase inhibitors is reported. The target molecules were obtained through highly stereoselective cycloadditions between sugriched allylic and homoallylic alcohols. This allowed the installation of a methyl group at C5 - a common feature of many natural hyacinthacines - with high control over the stereoselectivity. The new compounds inhibit amyloglucosidase from Aspergillus niger and β-glucosidase from almonds. Compound 1 is a competitive inhibitor of amyloglucosidase and shows a fair selectivity towards this enzyme. The presence of C5-Me substitution in indolizidines 2 and 3 slightly diminishes the inhibitory activity towards amyloglucosidase whereas it improves the inhibitory properties towards β-glucosidase. Cycloaddition between a carbohydrate-derived nitrone and suitable chemoenzymatically prepared enantioenriched allylic and homoallylic alcohols allowed the straightforward synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B. They inhibit amyloglucosidase from Aspergillus niger and β-glucosidase from almonds. Copyright

A chemoenzymatic total synthesis of the phytotoxic undecenolide (-)-cladospolide A.

An eleven-step synthesis of the title compound (1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)-9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.

A chemoenzymatic synthesis of the 12-membered macrolide (-)-cladospolide A

The enantiomerically pure cis-1,2-dihydrocatechol 7, which is obtained by microbial oxidation of chlorobenzene, has been converted, via a sequence of reactions including ring-closing metathesis and Yamaguchi lactonisation steps, into the natural product (-)-cladospolide A (1).