618902-48-0

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 80149-80-0 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate 
• 682812-50-6 N¹-[(2-trimethylsilyl)ethoxycarbonyl]-1,4-butanediamine 
• 121750-77-4 2-(trimethylsilyl)ethyl-p-nitrophenyl carbonate 
• 211512-13-9 N-(4-aminobutan-1-yl)-2-nitrobenzenesulfonamide 

Downstream Products

• 618902-51-5 {4-[(3-hydroxy-butyl)-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 133805-33-1 Agel 416 
• 133805-32-0 NPS 019 
• 618902-65-1 {4-[{3-[{3-[3-(4-tert-butoxy-phenyl)-2-butyrylamino-propionylamino]-propyl}-(2-nitro-benzenesulfonyl)-amino]-1-methyl-propyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-62-8 {4-[{3-[{3-[3-(4-tert-butoxy-phenyl)-2-butyrylamino-propionylamino]-propyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-54-8 {3-[{3-[{4-[3-(4-tert-butoxy-phenyl)-2-butyrylamino-propionylamino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-1-methyl-propyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester 
• 618902-59-3 {3-[{3-[{4-[3-(4-tert-butoxy-phenyl)-2-butyrylamino-propionylamino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester 
• 618902-52-6 {4-[{3-[(3-tert-butoxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-61-7 {4-[{3-[(3-amino-propyl)-(2-nitro-benzenesulfonyl)-amino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-63-9 [4-(3-{3-[3-(4-tert-butoxy-phenyl)-2-butyrylamino-propionylamino]-propylamino}-butylamino)-butyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-66-2 [4-(3-{3-[3-(4-tert-butoxy-phenyl)-2-butyrylamino-propionylamino]-propylamino}-1-methyl-propylamino)-butyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-64-0 {4-[{3-[(3-amino-propyl)-(2-nitro-benzenesulfonyl)-amino]-1-methyl-propyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 618902-53-7 {3-[{3-[(4-amino-butyl)-(2-nitro-benzenesulfonyl)-amino]-1-methyl-propyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester 
• 618902-58-2 {3-[{3-[(4-amino-butyl)-(2-nitro-benzenesulfonyl)-amino]-butyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Fukuyama-Mitsunobu alkylation in amine synthesis on solid phase revisited: N-alkylation with secondary alcohols and synthesis of curtatoxins

The Fukuyama-Mitsunobu amination strategy has emerged as an efficient means of N-alkylation of peptides and sulfonamides, as well as a method for synthesis of polyamines on solid phase. Here, an array of reagent combinations for solid-phase alkylation wit

Diols as Building Blocks in Solid-Phase Synthesis of Polyamine Toxins by Fukuyama-Mitsunobu Alkylation

Philanthotoxin-433 (PhTX-433) is a polyamine wasp toxin that antagonizes certain ionotropic receptors. In the present work three analogues of PhTX-433 were synthesized in good overall yields (27-31%) employing a Fukuyama-Mitsunobu strategy on solid phase.

The choice of phosphane reagent in Fukuyama-Mitsunobu alkylation: Intramolecular selectivity between primary and secondary alcohols in the preparation of asymmetric tetraamine building blocks for synthesis of philanthotoxins

Philanthotoxin-433 (PhTX-433) is a polyamine wasp toxin that antagonizes certain ionotropic receptors noncompetitively. Four analogues of PhTX-433, C-methylated in the polyamine chain, were synthesized from (RS)-1,3-butanediol, two diamine building blocks, and an activated/protected tyrosine derivative. Use of a phosphane reagent more bulky than trimethylphosphane gave a high intramolecular selectivity between primary and secondary hydroxy groups in the Fukuyama-Mitsunobu reaction. Thus, trimethylphosphane proved to be the only phosphane reagent that enabled alkylation of 2-nitrobenzenesulfonamides with a wide range of secondary alcohols, whereas tributylphosphane was selective for primary alcohol groups. This selectivity was utilized to obtain orthogonally protected, asymmetric, branched tetraamines, employed for solution-phase synthesis of philanthotoxin analogues. The branched philanthotoxin analogues thus obtained were tested in an electrophysiological assay using rat brain ionotropic glutamate receptors expressed in Xenopus laevis oocytes. Their potencies proved to be similar to the corresponding nonbranched analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.