477808-39-2Relevant academic research and scientific papers
An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides
Meng, Fanhua,Chen, Ning,Xu, Jiaxi
, p. 2548 - 2553 (2013/06/27)
An efficient method for the synthesis of N-Cbz-β- aminoalkanesulfonamides was described. N-Cbz-β-aminoalkanesulfona-mides were readily prepared in good yields from a variety of amino alcohols, including optically active ones, via N-Cbz protection with ben
Facile synthesis of hybrid sulfonophosphinodipeptides composing of taurines and 1-aminoalkylphosphinic acids
Meng, Fanhua,He, Fengdan,Song, Xiuqing,Zhang, Leilei,Hu, Wenxiang,Liu, Gang,Xu, Jiaxi
, p. 423 - 429 (2012/07/28)
Both sulfonopeptides and phosphonopeptides are important analogs of naturally occurring peptides and have been widely used as enzyme inhibitors and haptens for producing catalytic antibodies due to their tetrahedrally structural features. A series of hybr
Synthesis and biological evaluation of novel irreversible serine protease inhibitors using amino acid based sulfonyl fluorides as an electrophilic trap
Brouwer, Arwin J.,Ceylan, Tarik,Jonker, Anika M.,Linden, Tima Van Der,Liskamp, Rob M.J.
, p. 2397 - 2406 (2011/05/12)
We have designed and synthesized novel irreversible serine protease inhibitors containing aliphatic sulfonyl fluorides as an electrophilic trap. These substituted taurine sulfonyl fluorides derived from taurine or protected amino acids were conveniently s
Synthesis of β-aminoethanesulfonyl fluorides or 2-substituted taurine sulfonyl fluorides as potential protease inhibitors
Brouwer, Arwin J.,Ceylan, Tarik,Linden, Tima van der,Liskamp, Rob M.J.
scheme or table, p. 3391 - 3393 (2009/09/05)
Substituted taurine sulfonyl fluorides derived from taurine or protected amino acids are conveniently synthesized from β-aminoethanesulfonyl chlorides using KF/18-crown-6 or from β-aminoethanesulfonates using DAST.
Asymmetric synthesis of β-amino cyclohexyl sulfonates, β-sultams and γ-sultones
Enders, Dieter,Wallert, Stefan,Runsink, Jan
, p. 1856 - 1868 (2007/10/03)
An efficient asymmetric synthesis of β-aminocyclohexyl sulfonates, β-sultams and γ-sultones has been developed. The key step of the synthesis is the Lewis acid catalyzed aza-Michael addition of the enantiopure hydrazines SAMP [(S)-1] or RAMBO [(R,R,R)-2] to alkenylcyclohexyl sulfonates 3. This leads to β-hydrazino sulfonates 4a-k in moderate to good yields (41-85%) and diastereomeric excesses (de = 44-90%). The epimers were separated by preparative HPLC. Subsequent reductive N-N bond cleavage with BH 3·THF and protection of the resulting amines with CbzCl gave N-Cbz-protected β-aminocyclohexyl sulfonates 6a-k in moderate to good yields (38-68% over 2 steps) and high enantiomeric excesses (ee ≥ 96%). α-Alkylation of 6 with various electrophiles afforded α-alkyl-β -aminocyclohexyl sulfonates 10a-g in good to excellent yields (67-92%) and moderate to high diastereomeric excesses (de = 71-93%). After alkylation with allyl iodide, the first asymmetric iodosultonization was achieved with high selectivities. Compounds 6g-k were also cyclized in a four-step synthesis to highly enantio-enriched 3-substituted-1,2-thiazetidine 1,1-dioxides (β-sultams) 9a-e.
Efficient asymmetric synthesis of 3-substituted β-sultams
Enders, Dieter,Wallert, Stefan
, p. 5109 - 5111 (2007/10/03)
The asymmetric synthesis of 3-substituted 1,2-thiazetidine 1,1-dioxides by cyclization of β-amino-sulfonyl chlorides is reported. The synthesis is based on the aza-Michael addition of (R,R,R)-2-amino-3-methoxymethyl-2-azabicyclo[3.3.0]octane (RAMBO) to al
