21641-92-9

Usage

Uses

Building block for chiral tert-butyl substituted α-lactams, diols, and α-hydroxyketones.

InChI:InChI=1/C6H12O3/c1-6(2,3)4(7)5(8)9/h4,7H,1-3H3,(H,8,9)/t4-/m1/s1

Upstream product

• 20859-02-3 L-tert-Leucine 
• 815-17-8 trimethylpyruvic acid 
• 30263-65-1 1,1-dibromo-3,3-dimethylbutan-2-one 
• 446246-12-4 (1R,2S,6R,7S)-5-[(1R,2S)-2-hydroxy-3,3-dimethyl-1-(phenylsulfanyl)butyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-15-7 (1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-3,3-dimethyl-1-(phenylsulfanyl)butyl]-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 630-19-3 pivalaldehyde 
• 370066-57-2 (S)-2-Hydroxy-3,3-dimethyl-butyraldehyde 
• 75-97-8 3,3-dimethyl-butan-2-one 

Downstream Products

• 97869-13-1 (S)-3-hydroxy-4,4-dimethylpentan-2-one 
• 431069-66-8 (S)-1-benzylcarbamoyl-2,2-dimethyl-propanol 
• 300854-35-7 benzyl 2-hydroxy-3,3-dimethylbutanoate 
• 31612-63-2 (2S)-3,3-dimethylbutane-1,2-diol 
• 639074-95-6 3-{(2S)-4-(2,5-difluorophenyl)-1-[(2S)-2-hydroxy-3,3-dimethylbutanoyl]-2,5-dihydro-1H-pyrrol-2-yl}phenol 
• 884651-24-5 Phosphoric acid dibenzyl ester 3-[(S)-4-(2,5-difluoro-phenyl)-1-((S)-2-hydroxy-3,3-dimethyl-butyryl)-2,5-dihydro-1H-pyrrol-2-yl]-phenyl ester 
• 879324-93-3 (S)-1-[Benzyl-(2-hydroxy-ethyl)-amino]-3,3-dimethyl-butan-2-ol 
• 711028-26-1 (E)-(3S,10R,16S)-3-tert-Butyl-10-(4-methoxy-benzyl)-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 711028-24-9 (S)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-3,3-dimethyl-butyric acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(4-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 147252-87-7 (2S)-2-benzyloxy-3,3-dimethylbutanol 

Relevant academic research and scientific papers

Enantioseparation of racemic organic ammonium perchlorates by a silica gel bound optically active di-tert-butylpyridino-18-crown-6 ligand

Both enantiomers of the novel chiral di-tert-butylpyridino-18-crown-6 ligand (R,R)-7 and (S,S)-7 containing an allyloxy group on the pyridine subcyclic unit were prepared by the reaction of 4-allyloxy-2,6-pyridinedimethyl ditosylate 9 and the enantiomers of di-tert-butyl-substituted tetraethylene glycol (R,R)-8 and (S,S)-8 in the presence of a strong base. One of them, (R,R)-7, was covalently attached to silica gel, and this chiral stationary phase (CSP) separated four selected racemic organic ammonium perchlorates into their enantiomers by column chromatography.

Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation

N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.

Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation

A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring α-amino- or α-hydroxy acids, was found to provide high levels of both conversion and stereocontrol (up to 95:5 er) in intramolecular carbolithiation reactions, outperforming the benchmark ligand (?)-sparteine. The ligand could be used in a substoichiometric amount (0.25 equiv) without significant loss of enantioselectivity.

Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

Asymmetric hydrogenation reaction of alpha-ketoacids compound

The invention relates to the technical field of organic chemistry, especially to an asymmetric hydrogenation reaction of an alpha-ketoacids compound. The asymmetric hydrogenation reaction comprises a scheme shown in the description. In the scheme, R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, C1-C6 alkyl, or aralkyl; a substituent group is C1-C6 alkyl, C1-C6 alkoxy, or halogen; and the number of the substituent group is 1-3. In the scheme, M is a chiral spiro-pyridylamino phosphine ligand iridium complex having a structure shown in the description. In the structure, R is hydrogen, 3-methyl, 4-tBu, or 6-methyl.

Direct asymmetric hydrogenation of α-keto acids by using the highly efficient chiral spiro iridium catalysts

A new efficient and highly enantioselective direct asymmetric hydrogenation of α-keto acids employing the Ir/SpiroPAP catalyst under mild reaction conditions has been developed. This method might be feasible for the preparation of a series of chiral α-hydroxy acids on a large scale.

MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES

Provided are compounds of Formula I and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of virus infections, particularly hepatitis C infections.

Camphor-based Schiff base ligand SBAIB: An enantioselective catalyst for addition of phenylacetylene to aldehydes

A series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti(OiPr)4. This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to 92%). The corresponding (S)-propargylic alcohols were synthesized in good to high enantioselectivities (up to 91%) and excellent yields (up to 99%) using (-)-SBAIB-a, 41.

P2-P3 conformationally constrained ketoamide-based inhibitors of cathepsin K

An orally bioavailable series of ketoamide-based cathepsin K inhibitors with good pharmacokinetic properties has been identified. Starting from a potent inhibitor endowed with poor drug properties, conformational constraint of the P2-P3 linker and modifications to P1′ elements led to an enhancement in potency, solubility, clearance, and bioavailability. These optimized inhibitors attenuated bone resorption in a rat TPTX hypocalcemic bone resorption model.

α-Hydroxy carboxylic acids as ligands for enantioselective diethylzinc additions to aromatic and aliphatic aldehydes

The first examples of the enantioselective titanium-mediated diethylzinc additions to aromatic and aliphatic aldehydes catalyzed by optically active α-hydroxy acids are presented. The reactions proceed with very good yield and good asymmetric induction. Enantioselectivities up to 90% are obtained depending on ligand and aldehyde used. A stereochemical model for the reaction is proposed.