143564-89-0

Basic information

• Product Name: (2R,4R)-3-Benzyloxycarbonyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one
• Synonyms: (2R,4R)-3-BENZYLOXYCARBONYL-4-METHYL-2-PHENYL-1,3-OXAZOLIDIN-5-ONE;(2R, 4R) Z-5-OXAZOLIDINONE(2-PH, 4-ME);(2R,4R)-4-Methyl-5-oxo-2-phenyl-3-oxazolidinecarboxylic acid phenylmethyl ester;benzyl (2R,4R)-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate
• CAS NO: 143564-89-0
• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.33
• Mol File: 143564-89-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 509.982°C at 760 mmHg
• Flash Point: 262.228°C
• Appearance: /
• Density: 1.246
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• PKA: -3.12±0.60(Predicted)
• CAS DataBase Reference: (2R,4R)-3-Benzyloxycarbonyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-3-Benzyloxycarbonyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one(143564-89-0)
• EPA Substance Registry System: (2R,4R)-3-Benzyloxycarbonyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one(143564-89-0)

Safety Data

• Hazardous Substances Data: 143564-89-0(Hazardous Substances Data)

Usage

General Description

The chemical (2R,4R)-3-Benzyloxycarbonyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one, also known as (R,R)-BCMPO, is a white to off-white crystalline powder with a molecular formula of C17H17NO4. It is a chiral compound often used in organic synthesis as a reagent for the asymmetric dihydroxylation of alkenes. It is also used in the preparation of α-hydroxyimino esters, which are important intermediates in the synthesis of various pharmaceuticals and natural products. Additionally, (R,R)-BCMPO has been studied for its potential anticonvulsant and antinociceptive properties. Overall, (R,R)-BCMPO has important applications in organic chemistry and medicinal chemistry, making it a valuable compound in chemical research and drug development.

InChI:InChI=1/C18H17NO4/c1-13-17(20)23-16(15-10-6-3-7-11-15)19(13)18(21)22-12-14-8-4-2-5-9-14/h2-11,13,16H,12H2,1H3/t13-,16-/m1/s1

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 1142-20-7 N-Cbz-Ala 
• 501-53-1 benzyl chloroformate 
• 100-52-7 benzaldehyde 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 113806-26-1 sodium benzylidene-D-alanilate 

Downstream Products

• 143564-90-3 (2R,4R)-4-Benzylsulfanylmethyl-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 537040-12-3 (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one 
• 865468-88-8 C₂₂H₂₃NO₄ 
• 1445137-78-9 (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-(hex-5-enyl)oxazolidin-5-one 
• 1445137-77-8 (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-(but-3-enyl)oxazolidin-5-one 
• 1445137-76-7 (2R,4S)-benzyl 4-allyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylate 
• 1445137-75-6 (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-(4-pentenyl)oxazolidin-5-one 
• 1054648-05-3 C₁₄H₂₀N₂O₄ 
• 1364707-64-1 (2R,4S)-benzyl 4-(2-iodobenzyl)-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylate 
• 177546-82-6 {(R)-2-Benzylsulfanyl-1-[(R)-2-benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethylcarbamoyl]-1-methyl-ethyl}-carbamic acid benzyl ester 
• 177546-81-5 [(R)-2-Benzylsulfanyl-1-(2-benzylsulfanyl-ethylcarbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester 
• 191734-53-9 [(R)-2-Benzylsulfanyl-1-((R)-2-benzylsulfanyl-1-carbamoyl-1-methyl-ethylcarbamoyl)-1-methyl-ethyl]-carbamic acid benzyl ester 

Relevant articles and documents

COVALENT RAS INHIBITORS AND USES THEREOF

The disclosure features compounds, or pharmaceutically acceptable salts thereof, alone and in combination with other therapeutic agents, pharmaceutical compositions, and protein conjugates thereof, capable of modulating biological processes including Ras, and their uses in the treatment of cancers.

Method for preparing 2-methylserine

The invention relates to a method for preparing 2-methylserine, and mainly solves the technical problem of being long in route, complicated in operation, and not conducive to mass production of the existing synthetic method. The method comprises the following steps: Cbz-chiral alanine and Benzaldehyde dimethyl acetal are reacted under the action of thionyl chloride and zinc chloride, a reaction product is crystallized to obtain an intermediate 1, the intermediate 1 is reacted under cooperation of an alkaline reagent to obtain an intermediate 2, an intermediate 3 is obtained from the intermediate 2 by the action of lithium hydroxide, and the final product 2-methylserine is obtained from the intermediate 3 by palladium carbon catalytic hydrogenolysis. High purity 2-methylserine can be obtained by the method.

Design of cell-permeable stapled peptides as HIV-1 integrase inhibitors

HIV-1 integrase (IN) catalyzes the integration of viral DNA into the host genome, involving several interactions with the viral and cellular proteins. We have previously identified peptide IN inhibitors derived from the α-helical regions along the dimeric interface of HIV-1 IN. Herein, we show that appropriate hydrocarbon stapling of these peptides to stabilize their helical structure remarkably improves the cell permeability, thus allowing inhibition of the HIV-1 replication in cell culture. Furthermore, the stabilized peptides inhibit the interaction of IN with the cellular cofactor LEDGF/p75. Cellular uptake of the stapled peptide was confirmed in four different cell lines using a fluorescein-labeled analogue. Given their enhanced potency and cell permeability, these stapled peptides can serve as not only lead IN inhibitors but also prototypical biochemical probes or nanoneedles for the elucidation of HIV-1 IN dimerization and host cofactor interactions within their native cellular environment.