142035-70-9

Usage

Uses

Used in Pharmaceutical Research and Development:
(R)-Methyl 3-(((benzyloxy)carbonyl)aMino)butanoate is used as a building block in the pharmaceutical industry for the synthesis of various pharmaceuticals and biologically active compounds. Its unique chemical structure and properties make it a valuable intermediate in the development of new drugs.
Used in Organic Synthesis:
In the field of organic chemistry, (R)-Methyl 3-(((benzyloxy)carbonyl)aMino)butanoate is used as a key intermediate for the synthesis of complex organic molecules. Its chiral nature allows for the creation of enantiomerically pure compounds, which are essential in various applications, including the development of new drugs and specialty chemicals.
Used in the Production of Specialty Chemicals and Fine Chemicals:
(R)-Methyl 3-(((benzyloxy)carbonyl)aMino)butanoate is also utilized in the production of specialty chemicals and fine chemicals, where its unique properties and reactivity are harnessed to create high-value products for various applications, such as agrochemicals, fragrances, and dyes.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 105499-10-3 (R)-benzyl-(1-methyl-2-oxoethyl)carbamate 
• 121054-27-1 Methyl (+/-)-3-<(benzyloxycarbonyl)amino>butanoate 
• 100-51-6 benzyl alcohol 
• 623-43-8 methyl crotonate 
• 134430-97-0 methyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)butanoate 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 
• 501-53-1 benzyl chloroformate 
• 139243-54-2 (R)-3-aminobutanoic acid methyl ester hydrochloride 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 67-56-1 methanol 
• 68223-06-3 (3-diazo-1-(R)-methyl-2-oxopropyl)carbamic acid benzyl ester 
• 621-84-1 O-benzyl carbamate 

Downstream Products

• 323592-68-3 6-(S)-methylpiperazin-2-one 
• 1350922-81-4 (R)-benzyl [1-methyl-3-(4-morpholinyl)-3-oxopropyl]carbamate 
• 1350922-84-7 (R)-benzyl [1-(2-(2-aminoethyl)-1,3-dioxan-2-yl)propan-2-yl]carbamate 
• 1350922-82-5 (R)-benzyl [4-oxo-hex-5-en-2-yl]carbamate 
• 1350922-83-6 (R)-benzyl [6-(1,3-dioxoisoindolin-2-yl)-4-oxo-hexan-2-yl]carbamate 
• 1425667-32-8 (R,E)-benzyl [4-oxo-6-phenyl-hex-5-en-2-yl]carbamate 
• 1425667-34-0 (R,E)-benzyl [4-oxo-pentadec-5-en-2-yl]carbamate 
• 1425667-36-2 (R,E)-benzyl [4-oxo-heptadec-5-en-2-yl]carbamate 
• 1425666-89-2 (R)-benzyl [5-(diethoxyphosphoryl)-4-oxopentan-2-yl]carbamate 
• 947530-25-8 C₂₂H₂₅NO₄ 
• 1431706-23-8 C₂₂H₂₅NO₄ 
• 1425668-80-9 benzyl (7R,9R)-7-methyl-9-undecyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate 
• 1425668-82-1 benzyl (7R,9S)-7-methyl-9-undecyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate 
• 1425668-87-6 benzyl (2R,6R)-4,4-dimethoxy-2-methyl-6-nonylpiperidine-1-carboxylate 

Relevant academic research and scientific papers

Synthetic method of (R)-3- n-aminobutanol (by machine translation)

The invention belongs to, the field (R)- 3 - of pharmaceutical and chemical engineering, and particularly relates to a method for. preparing a product (R)- 3 - with good chemical purity, and optical, purity by, a, preparation method of a chiral drug midbody . (by machine translation)

Efficient synthesis of β'-amino-α, β-unsaturated ketones

A general and simple procedure to access chiral β'-amino-α, β-enones, in seven steps, from an α,β unsaturated ester has been described. The use of a Horner-Wadsworth-Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield.

Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D

Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.

Total synthesis and biological evaluation of grassypeptolide A

Herein, we describe in full our investigations into the synthesis of grassypeptolide A (1) in 17 linear steps with an overall yield of 11.3 %. In particular, this work features the late-stage introduction of sensitive bis(thiazoline) heterocycles and 31-membered macrocyclization conducted at the sterically congested secondary amide site in superb conversion (72 % yield). Biological evaluation indicated that grassypeptolide A significantly inhibited cancer cell proliferation in a dose-dependent manner. It induced cancer cell apoptosis, which was associated with increased cleavage of poly(ADP-ribose) polymerase (PARP) and decreased expression of bcl-2 and bcl-xL. Furthermore, grassypeptolide A also caused cell cycle redistribution by increasing cells in the G1 phase and decreasing cells in the S and G2 phases. In addition, cell cycle arrest was correlated with downregulation of cyclin D and upregulation of p27 and p21. Cytotoxic activity: Synthesis of grassypeptolide A, an anticancer marine cyclodepsipeptide, in 17 linear steps with an overall yield of 11.3 % is described (see figure). Subsequent biological evaluation indicated that grassypeptolide A significantly inhibited cancer-cell proliferation in a dose-dependent manner. Copyright

Stereoselective synthesis and in vivo evaluation of the analgesic activity of polysubstituted bispidines

Hetero-Michael addition on a chiral β'-amino α,β- unsaturated ketone gave, after some structural modifications, β,β'-diamino ketals. Mannich-type reactions of these diamines with an aldehyde led, with high diastereoselectivity, to trisubstituted piperidines. Another highly stereoselective Mannich cyclization, with an N-acyliminium ion generated in situ from the corresponding imide, allowed the preparation of original polycyclic bispidine derivatives. The antinociceptive effect of the three compounds prepared was evaluated in vivo by using the writhing test. If the biological results for the analgesic properties were disappointing, compared with the bispidine HZ2, which has a high affinity for opioid receptors, the modularity of the approach offered the possibility of introducing many substituents for new applications, which was promising because the bispidine core has been described to have many different activities. Total stereoselective synthesis of bispidine derivatives is achieved by using as two successive Mannich reactions key steps. This process constitutes a powerful approach toward the preparation of a polycyclic bispidine backbone with high enantioselectivity.

Synthesis of chiral non-racemic intermediates and Arg-Gly-Asp mimetics by CaLB-catalyzed resolution

The reactivity of both the ester and amine functions present in β-amino esters was tested in order to obtain the synthesis of enantiopure αvβ3 and α5β1 integrin ligands. CaLB successfully catalyzed both the enantioselective transesterification and the N-acylation of racemic β-amino esters, allowing the isolation of intermediates for the preparation of Arg-Gly-Asp (RGD) mimetic compounds. In particular, a CaLB-catalyzed amidation reaction with unprotected p-aminobenzylamine reduced the number of synthetic steps, thus avoiding protection and deprotection of the intermediate compounds. Following this procedure, RGD mimetics were isolated with high yields and enantiomeric purities.

GUANIDINO-SUBSTITUTED QUINAZOLINONE COMPOUNDS AS MC4-R AGONISTS

A variety of small molecule, guanidine-containing molecules capable of acting as MC4-R agonists are provided. The compounds are useful in treating MC4-R mediated diseases when administered to subjects. The compounds have the structure IA, IB, and IC where the values of the variables are defined herein.

On the enantioselective hydrogenation of isomeric β-acylamido β-alkylacrylates with chiral Rh(I) complexes - Comparison of phosphine ligands and substrates

The rhodium(I)-catalyzed enantioselective hydrogenation of E- and Z-configured β-acylamido β-alkylacrylates as well as of isomeric mixtures has been investigated. As ligands 1,2-bisphospholanes like DuPHOS, BPE and Me4-BASPHOS have been tested,