76465-91-3

Upstream product

• 60375-12-4 methyl trans-β-methyl-γ-carboxy-γ-valerolactone 
• 74-90-8 hydrogen cyanide 
• 6628-79-1 3-methyllevulinic acid 
• 86577-62-0 (2S,3S)-2-Hydroxy-2-methyl-3-(3-trimethylsilanyl-oxiranyl)-butyric acid methyl ester 
• 76405-12-4 S-tert-butyl hydrogen 4-hydroxy-3,4-dimethyl-1-thioglutarate acetate 
• 76405-10-2 S-tert-butyl hydrogen 4-hydroxy-3,4-dimethyl-1-thioglutarate acetate anhydride with acetic acid 
• 76405-17-9 S-tert-butyl O-<<(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl>methyl> 4-hydroxy-3,4-dimethyl-1-thioglutarate 4-acetate 
• 76405-13-5 S-tert-butyl γ-hydroxy-β,γ-dimethyl-δ-oxoimidazole-1-thiovalerate acetate 
• 55424-74-3 ethyl 3-methyl-4-oxopentanoate 
• 86577-63-1 (2R,3R)-5-Methoxy-2,3-dimethyl-tetrahydro-furan-2-carboxylic acid methyl ester 
• 86577-59-5 methyl 2,3-dimethyl-2-hydroxy-5-(trimethylsilyl)-4-pentenoate 
• 76465-88-8 (4S,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate 
• 76405-15-7 (4R,5S,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate 
• 76405-08-8 2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carbonitrile 

Downstream Products

• 60660-35-7 (2R-trans)-tetrahydro-2,3-dimethyl-5-oxo-2-furancarboxylic acid 
• 76405-16-8 (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 

Relevant academic research and scientific papers

Diastereoselective Reactions of Pyruvates with But-2-enyl Organometallic Compounds. Stereocontrol at the Tertiary Carbon Centre

The reaction of pyruvates (3) with but-2-enyl-9-borabicyclononane (2a) or its α-silyl and α-stannyl substituted derivatives (10) produced the threo-isomer stereoselectively; the latter reaction was applied to the synthes

Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid

Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea-H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.

Diastereodivergent Control in the Reactions of Allylic and Allenic Organometallic Reagents with Pyruvates

The reaction of crotyl-9-BBN (4a) with pyruvates (3) produced the threo (anti) isomer 5 either predominantly or exclusively.On the other hand, the reaction of allenic organometallic reagents 18 (M = B or Ti) gave the erythro (syn) isomer 20 preferentially