66057-15-6

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 7429-44-9 2-methoxycyclohexanone 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 135297-22-2 (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one 
• 175891-54-0 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1S,3S)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one 
• 244785-23-7 C₁₃H₁₅NO₄ 
• 135413-17-1 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one 

Relevant academic research and scientific papers

Preparation of silyl enol ethers using (bistrimethylsilyl)acetamide in ionic liquids

(matrix presented) Ionic liquids have been used for the preparation of silyl enol ethers from aldehydes and ketones with (bistrimethylsilyl)acetamide (BSA) in good yields.

The stereoselective synthesis of a key intermediate of the trinem antibiotic Sanfetrinem

By modulating the reactivity of the Lewis acid promoter it was possible to obtain, in a single stereoselective condensation step, the methoxyketone 7, an advanced intermediate in the synthesis of Sanfetrinem GV 104326.

Synthesis of esters of the potent anti-bacterial trinems and analogues

Coupling the silyl enol ether 5 and the β-lactam 9 (R = Me3Si) affords the ketones 13a-d. Compounds 13a, 13c and 13d are converted into the tricyclic lactams 16-20, 23-25. (Chemoenzymatic synthesis of optically pure silyl enol ether 5 gave access to homochiral lactams 23-25.) In addition the ketoazetidinones 13 are protected as the 1,3-oxazanes 30. A hydroxyethyl moiety is introduced into these oxazanes at C-11 with the desired stereochemistry using the Bouffard methodology, to afford the alcohols 32. Formation of the corresponding nitrobenzyl carbonate, deprotection and oxidation furnishes the ketones 35a and 35b, which are subsequently converted into the trinems 41a and 41b, respectively.

Reaction des vinylogues d'hemiacetals avec les ethers d'enols β-heterosubstitues : nouvelle synthese et cyclisation de composes δ-dicarbonyles α-heterosubstitues

Reaction of hemiacetal vinylogs 1 in the presence of boron trifluoride etherate with silyl enol ethers 2 or 3 prepared from α-heterosubstituted ketones 7 or 9 yields α-halo δ-dicarbonyl compounds 4 (X = Cl, Br) or α-methoxy δ-dicarbonyl compounds 5.When s