4946-37-6

Usage

InChI:InChI=1/C9H13NO/c11-9-7-5-3-1-2-4-6-8(7)10-9/h1-2,7-8H,3-6H2,(H,10,11)/b2-1-

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 5259-72-3 cyclo-octa-1,5-diene 

Downstream Products

• 261620-76-2 3-(tert-butoxycarbonyl)-3-azabicyclo[6.2.0]dec-7-ene-2-one 
• 112020-13-0 2-acetyl-9-(tert-butoxycarbonyl)-9-azabicyclo<4.2.1>nonane 
• 64285-06-9 (+/-)-Anatoxin A 
• 90741-53-0 t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate 

Relevant academic research and scientific papers

TETRAZINES FOR HIGH CLICK RELEASE SPEED AND YIELD

Disclosed herein are tetrazines substituted with groups that result in a high click conjugation yield and high click release yields. In some of several other aspects, the invention relates to combinations and kits comprising said tetrazines and a dienophile, preferably a trans-cyclooctene. In another aspect, the compounds, combinations, and kits are for use as a medicament.

COMPOUNDS FOR FAST AND EFFICIENT CLICK RELEASE

The invention disclosed herein relates to compounds, combinations, kits, and methods using same, for use in bioorthogonal release reactions. In particular, the compounds, combinations and kits of the invention can be used to achieve fast and efficient click release. Applications of the compounds, combinations, and kits of the invention include both in vitro and in vivo applications.

Efficient enzymatic routes for the synthesis of new eight-membered cyclic β-amino acid and β-lactam enantiomers

Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric β-amino acids [(1R, 2S)-9 and (1S, 2R)-9] and β-lactams [(1S, 8R)-3, (1R, 8S)-3 (1S, 8R)-4 and (1R, 8S)-7], through asymmetric acylation of (±)-4 (E > 100) or enantioselective hydrolysis (E > 200) of the corresponding inactivated (±)-3 or activated (±)-4 β-lactams, catalyzed by PSIM or CAL-B in an organic solvent. CAL-B-catalyzed ring cleavage of (±)-6 (E > 200) resulted in the unreacted (1S, 8R)-6, potential intermediate for the synthesis of enantiomeric anatoxin-a. The best strategies, in view of E, reaction rate and product yields, which underline the importance of substrate engineering, are highlighted.

Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: Potential starting compounds for the synthesis of anatoxin-a

9-Azabicyclo[6.2.0]-dec-4-en-10-one (±)-2, obtained from cyclooctadiene by addition of chlorosulfonyl isocyanate, was N-hydroxymethylated to (±)-3 and then resolved by lipase-catalysed asymmetric acylation of the primary OH group at the (S)-stereogenic centre. High enantioselectivity (E = 94) was observed when lipase PS and vinyl butyrate were used in di-iso-propyl ether at -15°C, resulting in the enantiomerically enriched ester 3a and alcohol 3b (e.e. ≥92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding β-lactams (1R,8S)-2a and (1S,8R)-2b (e.e. ≥93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (±)-2, (±)-7, 3a and 3b, followed by reduction, resulted in racemic 4-6 and 8 and enantiomeric 4a, 4b, 5a and 5b eight-membered cyclic β-amino acid derivatives.

Tandem reactions of anions: A short and efficient route to ±anatoxin-a

A new route to anatoxin-a (1) is reported which involves an anionically induced small ring opening/ring closure/ring opening cascade. The azabicyclo [4.2.1]nonane ring system of anatoxin-α is hence formed in one synthetic operation.

A Short and Efficient Route to (+/-) Anatoxin-a

A new route to Anatoxin-a 1 is reported which involves a tandem methyllithium mediated ring opening/intramolecular cyclisation as a key step to provide the required 2-acetyl-9-azabicyclononane ring structure in one synthetic operation.