99306-88-4

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 100-52-7 benzaldehyde 
• 63-91-2 L-phenylalanine 

Downstream Products

• 158554-91-7 (S)-3,4-dibenzylthiazolidine-2-thione 
• 1004316-38-4 (3-benzenesulfonyl-1-benzyl-4-tert-butoxycarbonylamino-2-hydroxy-5-phenyl-pentyl)-benzyl-carbamic acid tert-butyl ester 
• 168846-63-7 (2S,5S,3E)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-{[(1,1-dimethylethoxy)carbonyl]-N-benzyl}amino-1,6-diphenylhex-3-ene 
• 168846-62-6 (2S,5S)-2,5-bis-<(1,1-dimethylethoxy)carbonylamino>-1,6-diphenylhex-3-ene 
• 158380-73-5 N-(tert-butoxycarbonyl)-N-benzyl-L-phenylalaninol 
• 158380-76-8 N-benzyl-N-(tert-butoxycarbonyl)-L-phenylalaninal 
• 144141-82-2 (2S,4S,5S)-2,5-bis<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenyl-4-hydroxyhexane 
• 129491-63-0 (2S,3R,4R,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1,6-diphenyl-3,4-dihydroxyhexane 
• 129491-64-1 (2S,3S,4S,5S)-2,5-bis<<(tert-butyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane 
• 225939-65-1 (S)-N-(1-Allyloxy-3-phenylprop-2-yl)-benzylamin 
• 225939-69-5 (S)-N-(1-Allyloxy-3-phenylprop-2-yl)-benzylidenamin-N-oxid 
• 717127-84-9 (S)-2-N-benzyl-((S)-2-N-benzyl-N-[(S)-2-N-benzyl-N-{(S)-2-N-allyl-N-benzylaminopropyl}amino-3-methylbutyl]amino-4-methyl-pentyl)amino-3-phenyl-propan-1-ol 
• 717127-90-7 (S)-2-N-benzyl-((S)-2-N-benzyl-N-[(S)-2-N-benzyl-N-{(S)-2-N-benzylaminopropyl}amino-3-methylbutyl]amino-4-methyl-pentyl)amino-3-phenyl-propan-1-ol 
• 725228-02-4 (S)-2-[benzyl-(2-hydroxyethyl)amino]-3-phenylpropan-1-ol 

Relevant academic research and scientific papers

SAR studies of 4-acyl-1,6-dialkylpiperazin-2-one arenavirus cell entry inhibitors

Old World (Africa) and New World (South America) arenaviruses are associated with human hemorrhagic fevers. Efforts to develop small molecule therapeutics have yielded several chemical series including the 4-acyl-1,6-dialkylpiperazin-2-ones. Herein, we describe an extensive exploration of this chemotype. In initial Phase I studies, R1 and R4 scanning libraries were assayed to identify potent substituents against Old World (Lassa) virus. In subsequent Phase II studies, R6 substituents and iterative R1, R4 and R6 substituent combinations were evaluated to obtain compounds with improved Lassa and New World (Machupo, Junin, and Tacaribe) arenavirus inhibitory activity, in vitro human liver microsome metabolic stability and aqueous solubility.

Substituent effects in ring-chain tautomerism of the condensation products of non-racemic 1,2-aminoalcohols with aromatic aldehydes

The condensation of (S)-2-amino-2-phenylethanol or (S)-2-amino-3- phenylpropanol with substituted benzaldehydes in methanol or water led to crystalline products, which proved to exist in CDCl3 at 300 K as three-component (ringcis-ope

Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol

N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, β-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol.

Highly enantioselective synthesis of β-amino alcohols: A catalytic version

(Chemical Equation Presented) Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.

N-Alkyl oxazolidines as stereocontrol elements in asymmetric Diels-Alder cycloadditions of 9-substituted anthracene derivatives

Chiral 9-oxazolidinyl anthracene derivatives have been prepared as single diastereoisomers by condensation of 9-anthraldehyde with the appropriate N-alkyl amino alcohol. Asymmetric Diels-Alder cycloadditions of these with N-methyl maleimide proceeds in go

Asymmetric reduction of acetophenone using lithium aluminium hydride modified with some novel amino alcohol Schiff bases

Some new chiral Schiff bases have been prepared in good yields from various carbonyl groups and two 2-amino alcohols. LiAlH4 was treated with different equivalents of the Schiff bases. Enantioselective reduction of acetophenone is achieved in h

An iterative approach to novel polyamines via nucleophilic ring-opening of aziridinium ions with β-amino alcohols

An iterative procedure for the synthesis of a novel class of synthetic polyamines has been developed, utilising the regioselective ring-opening of aziridinium ion intermediates; facile N-allyl deprotection of intermediate polyamines allows the rapid const

Preparation of chiral heterocyclic esters of β-amino acids

Chiral β-amino alcohols were successively prone to N-benzylation, O-allylation and oxidation of the resulting benzylamino group to give nitrones 3 which on hydrolysis afforded chiral hydroxylamines HO-NH-CH(R)-CH2-O-CH2-CH=CH2 ((S)-4: R = Me, Bn, iPr, (R)-4: R = Et). Swern oxidation of methyl 2,2-dimethyl-3-hydroxypropionate (16) and treatment of the resulting aldehyde 17 with hydroxylamines (S)-4b (R = Bn) or (R)-4d (R = Et) provided nitrones 18 that underwent an intramolecular 1,3-dipolar cycloaddition on heating yielding the bicyclic β-amino-acid esters 19b and ent-19d, respectively. Reductive cleavage of the N,O-bond of compounds 19 afforded the eight-membered ring compounds 20b and ent-20d, respectively. N-Benzylalaninol (22) was treated with β-bromo-methacrylate to give the amino alcohol 23. Swern oxidation and subsequent treatment with N-tert-butylhydroxylamine provided the bicyclic ester 26a (R = t-Bu) via the corresponding nitrone 24. Oxime 25 was prepared in an analogous way as 24 with unsubstituted hydroxylamine. It underwent an intramolecular 1.3-dipolar cycloaddition yielding 26b on heating in toluene. Reduction of 26a afforded the pyrrolidine-carboxylic ester 27a.

Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides

Four examples of the chiral thiazolidin-2-one 1,1-dioxides 5 have been prepared by reaction of the appropriate amino alcohols 11 with CS2 in aqueous sodium hydroxide to give the thiazolidine-2-thiones 12, followed by oxidation with KMnO4 under phase-transfer conditions in the presence of benzoic acid, either directly or via the thiazolidin-2-ones 13. Upon flash vacuum pyrolysis (FVP) at 650°C, 5a-c decompose mainly by loss of SO2 to give an alkene and benzyl isocyanate together with other products from fragmentation of the N-benzyl group. A significant minor pathway involves net loss of CO2 and water to give the 2-phenyl-4,5-dihydrothiazoles 21 together with their aromatisation products 22 and 23. A mechanism for this new heterocyclic transformation is proposed involving initial expansion to a cyclic carbamic-sulnnic anhydride (2,1,4-oxathiazin-3-one 1-oxide). The fully assigned 13C NMR spectra are presented for 5, 12 and 13 and the 33S NMR spectrum has been obtained for 5c.

Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors

The Julia's olefination reaction between the sulfone derivative (10) and the aldehyde (13) (both obtained from L-phenylalanine) followed by debenzylation led to the formation (2S,5S,3E)-2,5-bis-[(1,1-dimethyl ethoxy)-carbonyl]amino-1,6-diphenylhex-3-ene (