132684-60-7

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-L-tert-leucine is used as a reactant for the discovery of potent antagonists of the antiapoptotic protein X-linked inhibitor of apoptosis (XIAP). This application is significant in the treatment of cancer, as it helps in the development of new therapeutic strategies to target and inhibit XIAP, thereby promoting apoptosis and reducing tumor growth.
Used in Chemical Catalysts:
Fmoc-L-tert-leucine is also used as a reactant in the preparation of phosphino dipeptide derivatives, which serve as ligands in copper-phosphine catalysts. These catalysts are essential for the asymmetric conjugate addition of alkylzinc reagents to unsaturated ketones, a crucial reaction in the synthesis of various pharmaceuticals and fine chemicals. The use of Fmoc-L-tert-leucine in this context contributes to the development of more efficient and selective catalysts for asymmetric reactions, ultimately leading to the production of enantiomerically pure compounds with improved properties and applications.

InChI:InChI=1/C21H23NO4/c1-21(2,3)18(19(23)24)22-20(25)26-12-17-15-10-6-4-8-13(15)14-9-5-7-11-16(14)17/h4-11,17-18H,12H2,1-3H3,(H,22,25)(H,23,24)/t18-/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 471-50-1 2-L-amino-3,3-dimethylbutyric acid 
• 20859-02-3 L-tert-Leucine 
• 24324-17-2 9-Fluorenylmethanol 
• 139163-43-2 (S)-2-amino-3,3-dimethylbutanoic acid hydrochloride 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 1231171-63-3 DOTA-NLys⁽⁸⁾-Lys⁽⁹⁾-Pro⁽¹⁰⁾-Tyr⁽¹¹⁾-Tle⁽¹²⁾-Leu⁽¹³⁾ 
• 1299449-87-8 C₂₄H₃₆IN₃O₅ 
• 1299449-81-2 C₁₈H₂₆IN₃O₃ 
• 1299449-84-5 C₂₄H₃₇IN₄O₄ 
• 1299449-85-6 C₂₃H₃₅IN₄O₄ 
• 1299449-88-9 C₂₉H₄₆IN₅O₅ 
• 1299449-89-0 C₂₈H₄₄IN₅O₅ 
• 1299449-79-8 C₁₉H₂₈IN₃O₃ 
• 1299449-93-6 C₁₈H₂₄IN₃O₃ 
• 1299449-94-7 C₂₄H₃₅IN₄O₄ 
• 1299449-69-6 C₂₂H₂₆IN₃O₃ 
• 1299449-77-6 C₁₉H₂₈IN₃O₃ 
• 1299449-71-0 C₂₁H₂₄IN₃O₃ 
• 1299449-83-4 C₂₅H₃₉IN₄O₄ 

Relevant academic research and scientific papers

ATAZANAVIR (ATV) ANALOGUES FOR TREATING HIV INFECTIONS

The invention provides a compound of Formula I: or a pharmaceutically acceptable salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of Formula I, processes for preparing compounds of Formula I, the compound of formula (I) for use in therapeutic methods for treating the proliferation of the HIV virus, treating AIDS or delaying the onset of AIDS symptoms in a mammal using compounds of Formula I. Preferred compounds are N-[(2S) -1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino) -3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(phenyl) methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate atazanavir (ATV) analogues substituted by several heterocycles, such as e.g. pyrazole (Rl); e.g. oxetane (substituent of X2); e.g. pyridine or pyrimidine (X1); e.g. piperazine or 3,8-diazabicyclo[3.2.1]octan (X2).

Chiral oxazoline NNP type ligands as well as synthesis method and application thereof

The invention relates to chiral oxazoline NNP type ligands as well as a synthesis method and an application thereof. The ligands adopt the structure shown in general formula 1 or 2. During preparation, a chiral ligand 1 and a chiral ligand 2 are prepared from Fmoc-Cl and a chiral amino acid compound 3 used as initial raw materials through multi-step reactions. The ligands can be applied to catalytic synthesis of chiral beta ketone ester fluoride and synthesis of propanedione derivatives and chiral malonate derivatives through palladium-catalyzed asymmetric allyl substitution reactions. Compared with the prior art, the reaction condition is mild, operation is easy, repeatability is good, mass preparation can be realized, and the prepared catalyst has higher ee value and yield when applied to beta ketone ester fluoridation and palladium-catalyzed asymmetric allyl substitution reactions.

Ureidopeptide-based Bronsted bases: Design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles

The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Bronsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis. Learning from peptides: A concise route for the catalytic enantioselective synthesis of β-amino nitriles has been achieved by using ureidopeptide-based Bronsted bases as catalysts in the Mannich reaction of N-Boc imines and (arylsulfonyl)acetonitriles (see scheme; Boc=tert-butoxycarbonyl, napht=naphthyl, TMS=trimethylsilyl).

Catalytic enantioselective synthesis of tertiary thiols from 5h-thiazol-4-ones and nitroolefins: Bifunctional ureidopeptide-based bronsted base catalysis

Fully loaded: The ureidopeptide-based bifunctional Bronsted base 1 efficiently promotes the first direct catalytic Michael reaction of α-mercapto carboxylate surrogates with nitroolefins involving a fully substituted α-carbon atom construction. Copyright

Catalytic asymmetric acylcyanation of imines

(Chemical Equation Presented) The less problematic acetyl cyanide can be used instead of toxic HCN for the highly enantioselective acyl-Strecker-type reaction. In the presence of an N-benzylimine and a catalytic amount of Jacobsen's catalyst 1, the desire

Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles

(Chemical Equation Presented) Homochiral α-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde. The key feature of the sequence is a highly selective tandem Mitsunobu/3,3-sigmatropic rearrangement of hydrazoic acid that procures enantiomerically enriched allylic azides. The sequence is either terminated by oxidative cleavage to provide amino acids or by ring-closing metathesis to provide heterocycles or carbocycles bearing nitrogen.

Solid-phase synthesis and opioid activities of [D-Ala2]Deltorphin II analogs

[D-Ala2]Deltorphin II (DL-II) analogs having various aliphatic amino acids at positions 5 and 6 were synthesized by a solid-phase method and their opioid activities on electrically induced guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations were determined. During the synthesis of an analog, [tert-leucine(Tle)5,6]DL-II, we encountered difficulty in the coupling reaction between Tle5 and Tle6 with the usual diisopropylcarbodiimide (DIPCDI)-mediated tert-butoxycarbonyl (Boc) strategy, though the other analogs could be successfully synthesized. We found that the fluorenylmethoxycarbonyl (Fmoc)-Tle/DIPCDI/1-hydroxybenztriazole method was very useful for the synthesis of such a peptide having a sterically hindered sequence. Acid hydrolysis studies of the synthetic analogs suggested that the steric hindrance of consecutive aliphatic amino acid sequences depend upon the degree of branching at the β-carbon atom of the amino acids. In the MVD assay, two analogs, [Ala5,6] and [Tle5,6]DL-II showed remarkably low potencies while other analogs with Nva5,6, Nle5,6, Ile5,6, Leu5,6 and Mle5,6 substituted for Val5,6(DL-II) showed comparable or slightly lower potencies than DL-II. In the GPI assay, no remarkable changes in potency were observed between DL-II and this series of analogs. Conformational aspects of synthetic analogs were examined by comparing the circular dichroism spectra.

Method for treating inflammation and compounds and compositions suitable for use therein

The present invention relates to a method of treating an inflammatory condition, and to compounds and composition suitable for use in such a method, which compounds have the Formula: STR1 wherein: X is methylene, ethylene, ethyleneoxy, or oxygen; Q is STR2 where C' is a residue of a lipophilic amino acid, and Y is --CO2 H, --CH2 OH, --CONR1 R2, or --CO2 R1 where R1 and R2 hydrogen, alkyl, or aryl; R3 and R4 are, independently, hydrogen, alkyl or aryl; and A and B are, independently, hydrogen, fused phenyl, alkyl, aryl, alkaryl, aralkyl, alkoxy, alkoxyalkyl, halogen, or nitro; or pharmaceutically acceptable salts thereof.

Site-specific incorporation of non-natural residues into peptides: Effect of residue structure on suppression and translation efficiencies

A systematic survey of the structural requirements for biosynthetic incorporation of non-natural residues into a polypeptide is presented. Relative translation efficiencies for a series of 12 semi-synthetic acylated suppressor tRNAs ranged from 0 to 91% depending on the structure of the residue incorporated.