152298-88-9

Upstream product

• 6600-40-4 L-Norvaline 
• 137428-32-1 (2S)-2-[bis(phenylmethyl)amino]-1,4-butanediol 
• 152298-86-7 (S)-1-(3-N,N-dibenzylamino-4-tert-butyldimethylsilyloxy)butylmethanesulfonate 
• 161531-12-0 (S)-1-(3-N,N-dibenzylamino-4-hydroxy)butylmethanesulfonate 
• 100-39-0 benzyl bromide 
• 22724-81-8 L-norvalinol 
• 152298-87-8 (S)-N,N-dibenzyl-2-(1-tert-butyldimethylsilyloxy)pentylamine 
• 159497-65-1 N,N-dibenzylasparaginic acid dibenzyl ester 

Downstream Products

• 599207-03-1 [(S)-1-((R)-1-Hydroxy-ethyl)-butyl]-carbamic acid tert-butyl ester 
• 378752-99-9 (S)-2-(N,N-Dibenzylamino)-pentanal 

Relevant academic research and scientific papers

Palladium-N-heterocyclic carbene (NHC)-catalyzed asymmetric synthesis of indolines through regiodivergent C(sp3)-H activation: Scope and DFT study

Two bulky, chiral, monodentate N-heterocyclic carbene ligands were applied to palladium-catalyzed asymmetric C-H arylation to incorporate C(sp3)-H bond activation. Racemic mixtures of the carbamate starting materials underwent regiodivergent reactions to afford different trans-2,3- substituted indolines. Although this CAr-Calkyl coupling requires high temperatures (140-160°C), chiral induction is high. This regiodivergent reaction, when carried out with enantiopure starting materials, can lead to single structurally different enantiopure products, depending on the catalyst chirality. The C-H activation at a tertiary center was realized only in the case of a cyclopropyl group. No C-H activation takes place alpha to a tertiary center. A detailed DFT study is included and analyses of methyl versus methylene versus methine C-H activation is used to rationalize experimentally observed regio- and enantioselectivities.

Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri

4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors

In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused

Antitumoral compounds

New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR′, SH, SR′, SOR′, SO2R′, NO2, NH2, NHR′, N(R′)2, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form =O; Y is NR1, OR1, PR1, SR1, or halogen, wherein the number of substituents R1 is selected to suit the valency and each R1 is independently selected of H, OH, C(=O)R′, P(=O)R′R″, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR′, SH, SR′, SOR′, SO2R′, NO2, NH2, NHR′, N(R′)2, NHC(O)R′, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form =O; z is 0 to 25; y is to 0 to 20; R2 is H, C(=O)R′, P(=O)R′R″, S(=O)R′R″, S(=O)2R′, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 Alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; R3 is H, C(=O)R′, P(=O)R′R″, S(=O)R′R″, S(=O)2R′, substituted or unsubstituted C1-C18 alklyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; each of the R′, R″ groups is independently selected from the group consisting of H, OH, NO2, NH2, SH, CN, halogen, =O, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C16-C24 2-amino-3-hydroxyalkane or a C16-C24 2-amino-3-hydroxyalkene.

2-Dibenzylaminobutane-1,4-diol: An Effective Chiral Building Block for the Synthesis of 1,2-Amino Alcohols

Regioselective activation and protection of the chiral building block 1, readly available from L-aspartic acid, leads to the key intermediate 8.Employing classical nucleophiles, heterocyclic anions or organocuprates, 8 could be transformed into the displa

PRACTICAL EPC SYNTHESIS OF 1,2- AND 1,3-AMINO ALCOHOLS

An efficient synthesis of enantiomerically pure 1,2- and 1,3-amino alcohols (4,10) through the key intermediates 2 and 8a,b, obtained from L-aspartic acid, is reported.Using 4d as an example it is shown that the products can serve as percursors for unusual amino aldehydes and nonproteinogenic amino acids.