474023-97-7

Usage

Uses

Used in Organic Synthesis:
(2S)-amino-4-(tert-butyldimethylsilanyloxy)butanoic acid is used as a protective agent for alcohols and amines during organic synthesis. The TBDMS group allows chemists to prevent unwanted side reactions, ensuring cleaner reactions and higher yields of desired products.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (2S)-amino-4-(tert-butyldimethylsilanyloxy)butanoic acid is utilized as a building block for the development of new drugs. Its unique structure and reactivity make it a promising candidate for the synthesis of novel therapeutic agents, potentially leading to the discovery of innovative treatments for various diseases and conditions.

Upstream product

• 672-15-1 L-homoserine 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1333332-17-4 N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-homoserine 
• 1380298-40-7 C₂₂H₃₉NO₆SSi 
• 1380243-35-5 (R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate 

Relevant academic research and scientific papers

INHIBITORS OF PEPTIDYL ARGININE DEIMINASE (PAD) ENZYMES AND USES THEREOF

The present application relates to a-substituted amino acid compounds of the Formula (I), compositions comprising these compounds and their use, in particular for the treatment of diseases, disorders or conditions characterized by or associated with the hypercitrullination of proteins by peptidyl arginine deiminase (PAD) enzymes.

Noncovalent Protein Arginine Deiminase (PAD) Inhibitors Are Efficacious in Animal Models of Multiple Sclerosis

Peptidyl arginine deiminases have been shown to be hyperactive in neurodegenerative diseases including multiple sclerosis. An α-amino acid-based core structure, derived from a hydantoin core, with unique heterocycles on the side chains were synthesized as potential noncovalent inhibitors of PAD enzymes. Among the various heterocycles investigated, compound 23, carrying an imidazole moiety, exhibited the highest potency in this series with some selectivity for PAD2, and was further investigated in vivo. Pharmacokinetics in mice suggested the Cmax to be 12.0 ± 2.5 μg/mL and 170 ± 10 ng/mL in the serum and brain, respectively, when compound 23 was administered at 50 mg/kg via single dose ip. At the same dose, compound 23 also reversed physical disability and cleared the brain of T-cell infiltration in an EAE mouse model of multiple sclerosis (MS). This novel series of compounds show promise for further development as disease modifying agents for the potential treatment of MS.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

Efficient synthesis of sitagliptin phosphate, a novel DPP-IV inhibitor, via a chiral aziridine intermediate

Sitagliptin phosphate, a novel DPP-IV inhibitor of T2DM, has been synthesized via 12 linear steps, in an overall yield of 26%. The key step is the coupling reaction of 2,4,5-trifluorophenylmagnesium bromide with a chiral aziridine derivative, which was prepared from l-homo-serine by simple steps.

INHIBITORS OF IKK-BETA SERINE-THERONINE PROTEIN KINASE

Cyclopentyl(2S,4E)-2-amino-5-{3-[4-carbamoyl-5(carbamoylamino)-2-thienyl]phenyl}pent-4-enoate; Cyclopentyl 5-{3-[4-carbamoyl-5-(carbamoylamino)-2-thienyl]phenyl}-L-norvalinate; Cyclopentyl(2S,4E)-2-amino-5-{3-[4-carbamoyl-5-(carbamoylamino)-2-thienyl]-5-m

α-Conotoxin ImI incorporating stable cystathionine bridges maintains full potency and identical three-dimensional structure

The two disulfide bonds of α-conotoxin ImI, a peptide antagonist of the α7 nicotinic acetylcholine receptor (nAChR), were systematically replaced with isosteric redox-stable cystathionine thioethers. Regioselective thioether formation was accomplished on solid support through substitution of a γ-chlorohomoalanine by an intramolecular cysteine thiol to produce hybrid thioether/disulfide analogues (2 and 3) as well as a dual cystathionine analogue (4) that were found to be structurally homologous to α-conotoxin ImI by 1H NMR. The antagonistic activity at the α7 nAChR of cystathionine analogue 3 (pIC50 = 6.41 ± 0.09) was identical to that of α-conotoxin ImI (1, pIC50 = 6.41 ± 0.09), whereas those of 2 (pIC50 = 5.96 ± 0.09) and 4 (pIC 50 = 5.89 ± 0.09) showed a modest decrease. The effect of oxidation of the thioethers to sulfoxides was also investigated, with significant changes in the biological activities observed ranging from a >30-fold reduction (2S=O) to a 3-fold increase (3S=OB) in potencies.

PYRROLO [2, 3-D] PYRIMIDINES AS INHIBITORS OF HSP90

The invention provides a compound compound which is (a) a pyrrolopyrimidine derivative of formula (I) or a tautomer thereof, or (b) a pharmaceutically acceptable salt, N-oxide, hydrate or solvate thereof: wherein R1, R2, R3/sup

Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein

Nα-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC50) of 0.6 and 0.2 μM, which are 2-and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.

INHIBITORS OF IKK-β SERINE-THREONINE PROTEIN KINASE

Cyclopentyl (2S,4E)-2-amino-5-{3-[4-carbamoyl-5 (carbamoylamino)-2-thienyl]phenyl}pent-4-enoate; Cyclopentyl 5-{3-[4-carbamoyl-5-(carbamoylamino)-2-thienyl]phenyl}-L-norvalinate; Cyclopentyl (2S,4E)-2-amino-5-{3-[4-carbamoyl-5-(carbamoylamino)-2-thienyl]-