458560-69-5

Upstream product

• 100-52-7 benzaldehyde 
• 65943-49-9 (S)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-propan-1-ol 
• 6940-80-3 (S)-N-benzylalaninol 

Downstream Products

• 458560-73-1 (S)-N-benzyl-2-amino-1-fluoropropane 
• 458560-71-9 (S)-3-benzyl-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide 
• 149341-31-1 (S)-(+)-2-benzylaminoheptane 

Relevant academic research and scientific papers

Facile synthesis of β-amino disulfides, cystines, and their direct incorporation into peptides

Herein, we report a simple and efficient methodology for the synthesis of β-amino disulfides by regioselective ring opening of sulfamidates with benzyltriethylammonium tetrathiomolybdate [BnNEt3] 2MoS4. Stability and reactivity of different protecting groups under the reaction conditions have been discussed. This methodology has also been extended to serine and threonine derived sulfamidates to furnish cystine and 3,3′-dimethyl cystine derivatives. Georg Thieme Verlag.

Fluoroamines via chiral cyclic sulfamidates

N-benzyl [1,2,3]-oxathiazolidine 2,2-dioxides (cyclic sulfamidates) were synthesized from their corresponding β-amino alcohols and used as substrates in fluorination reactions with tetrabutylammonium fluoride (TBAF). After desulfonation of the intermediates, the N-benzyl fluoroamines were debenzylated by transfer hydrogenolysis with Pd/C to yield (S) and (R)-2-amino-1-fluoropropanes (2b and 3b, respectively, both with 95% ee). The reactions were carried out on multi-gram scale without the need for chromatographic purification of the intermediates. In the presence of carbonate, the (S)- and (R)-N-benzylfluoroamines underwent intramolecular cyclizations in which fluoride was displaced to yield cyclic carbamates 13 and 14.

New carbon-carbon bond forming reactions of cyclic sulfate esters and cyclic sulfamidates

Carbon-carbon bonding forming reactions of two cyclic sulfate esters and a cyclic sulfamidate are reported, the former with lithium dianions to give substituted tetrahydrofuran derivatives with displacement of sulfate, and the latter undergoes ring-openin