168297-85-6

Basic information

• Product Name: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone
• Synonyms: (S)-(-)-4-BENZYL-5,5-DIMETHYL-2-OXAZOLIDINONE;(S)-(+)-4-BENZYL-5,5-DIMETHYL-2-OXAZOLIDINONE;(S)-4-BENZYL-5,5-DIMETHYL-OXAZOLIDIN-2-ONE;(S)-(-)-4-BENZYL-5,5-DIMETHYL-2-OXA- ZOLIDINONE, 98% (99% EE/HPLC);2-Oxazolidinone,5,5-dimethyl-4-(phenylmethyl)-,(4S)-(9CI);(S)-4-Benzyl-5,5-dimethyl-2-oxazolidinone,99%e.e.
• CAS NO: 168297-85-6
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.25
• Product Categories: N-BOC;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 168297-85-6.mol

Chemical Properties

• Melting Point: 65-68 °C(lit.)
• Boiling Point: 385ºC at 760 mmHg
• Flash Point: 186.7ºC
• Appearance: /
• Density: 1.085 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.519
• PKA: 12.86±0.60(Predicted)
• CAS DataBase Reference: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone(168297-85-6)
• EPA Substance Registry System: (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone(168297-85-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 168297-85-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone is used as a chiral auxiliary in the pharmaceutical industry for its ability to control the stereochemistry of reactions, which is crucial in the synthesis of enantiomerically pure compounds. This ensures the desired biological activity and reduces potential side effects associated with the unwanted enantiomer.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone is employed as a chiral auxiliary to synthesize enantiomerically pure agrochemicals. This helps in developing more effective and environmentally friendly products by targeting specific pests while minimizing the impact on non-target organisms.
Used in Fine Chemicals Industry:
(S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone is utilized as a chiral auxiliary in the fine chemicals industry for the synthesis of enantiomerically pure compounds with specific properties. This is important in the development of high-value specialty chemicals, such as fragrances, dyes, and other performance chemicals.
Used in Asymmetric Synthesis:
(S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone is used as a chiral auxiliary in asymmetric synthesis to control the stereochemistry of reactions, leading to the formation of enantiomerically pure products. This is essential in the development of new drugs, agrochemicals, and other fine chemicals with improved selectivity and potency.
Used in Chemical Synthesis and Drug Development:
Due to its unique structure and chiral nature, (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone is a versatile and important compound for chemical synthesis and drug development. It plays a crucial role in the discovery and optimization of new molecules with potential therapeutic and commercial applications.

InChI:InChI=1/C12H15NO2/c1-12(2)10(13-11(14)15-12)8-9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,13,14)/t10-/m0/s1

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 168297-81-2 N-<(S)-1-benzyl-2-hydroxy-2-methylpropyl>-2,2,2-trichloroethanamide 
• 204851-63-8 (R)-2-Benzyl-3-hydroxy-3-methyl-butyric acid 
• 168297-89-0 (S)-3-(2',2'-dimethyl-1'-oxopropyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 250280-60-5 (4S)-4-Benzyl-5,5-dimethyl-3-[(2S)-2-methyl-6-heptenoyl]-1,3-oxazolidin-2-one 
• 320606-07-3 (S)-3-(2'-benzyl-3'-phenylpropionyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 846542-14-1 (2'S,3'S,4S,4'R,5'R)-4-benzyl-3-[2',4'-bis(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one 
• 937204-00-7 C₂₄H₃₉NO₄Si 
• 623-33-6 glycine ethyl ester hydrochloride 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 63-91-2 L-phenylalanine 
• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 320606-12-0 (S)-4-benzyl-N-butanoyl-5,5-dimethyl-1,3-oxazolidin-2-one 
• 170918-41-9 (S)-2-amino-3-phenyl-1,1-dimethylpropanol 

Downstream Products

• 168297-89-0 (S)-3-(2',2'-dimethyl-1'-oxopropyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 250280-59-2 (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one 
• 412050-37-4 (4S)-4-benzyl-3-({[6-(1,4-dioxaspiro[4.5]dec-6-en-7-yl)hex-2-ynyl]dimethylsilyl}methyl)-5,5-dimethyloxazolidin-2-one 
• 320606-10-8 (S)-3-(4'-methylpentanoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 320606-12-0 (S)-4-benzyl-N-butanoyl-5,5-dimethyl-1,3-oxazolidin-2-one 
• 618437-03-9 (4S)-4-benzyl-5,5-dimethyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 630390-08-8 (S)-(-)-4-benzyl-5,5-dimethyl-3-(7-methyl-oct-6-enoyl)-oxazolidin-2-one 
• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 496877-70-4 (S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 768392-19-4 (S)-4-benzyl-3-(2'-bromoacetyl)-5,5-dimethyloxazolidin-2-one 
• 618436-90-1 (S)-3-((E)-but-2-enoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 937204-13-2 C₁₈H₂₃NO₄ 
• 937203-99-1 C₂₄H₃₇NO₄Si 
• 937204-00-7 C₂₄H₃₉NO₄Si 

Relevant articles and documents

Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters

Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed reactivity and the outstanding stereocontrol. Importantly, the resultant compounds can be easily converted into ligands for asymmetric and catalytic transformations.

Synthesis of enantioenriched α-chiral bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficie

Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives

The first asymmetric total synthesis of ophiorrhisine A (1), a new cyclic tetrapeptide isolated from Ophiorrhiza nutans, was accomplished via an intramolecular aromatic nucleophilic substitution reaction (IMSNAr) of a linear tripeptide to construct a 14-membered paracyclophane ring, resulting in confirmation of its structure and absolute configuration. The structure-activity relationship study of 1 and its derivatives demonstrated that some derivatives possessed cytotoxicity toward human cancer cell lines A549, HT29, and HCT116.

Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen

A novel approach to synthesize enantiomerically pure α-hydroxy carboxylic derivatives is reported. A highly stereoselective oxidation of titanium(IV) enolates from chiral N -acyloxazolidinones is performed with oxygen under simple experimental conditions

Stereoselective aminoxylation of biradical titanium enolates with TEMPO

A highly efficient and straightforward aminoxylation of titanium(IV) enolates from (S)-N-acyl-4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-ones with TEMPO has been developed. A wide array of functional groups on the acyl moiety, including alkyl and aryl substituents, olefins, esters, or α-cyclopropyl, as well as α-trifluoromethyl groups, are well tolerated. This transformation can therefore produce the α-aminoxylated adducts in excellent yields with high diastereomeric ratios (d.r.). In turn, parallel additions to the α,β-unsaturated N-acyl counterparts give the corresponding γ-adducts with complete regioselectivity in moderate to good yields. Removal of the piperidinyl moiety or the chiral auxiliary converts the resultant adducts into enantiomerically pure α-hydroxy carboxyl derivatives, alcohols, or esters in high yields under mild conditions. Finally, a new mechanistic model based on the biradical character of the titanium(IV) enolates has been proposed.

Asymmetric radical addition of TEMPO to titanium enolates

A mild method for a-hydroxylation of N-acyl oxazolidinones by asymmetric radical addition of the 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO) radical to titanium enolates was developed. The high diastereoselectivity and broad scope of the reaction show synthetic utility for the a-hydroxylation of substrates that are not tolerant to strongly basic conditions.

Dihydroxylation-based approach for the asymmetric syntheses of hydroxy-γ-butyrolactones

A method of preparing enantiopure hydroxy-γ-butyrolactones containing multiple contiguous stereocenters in high yield with good diastereoselectivity has been developed. Osmium tetroxide mediated dihydroxylation of a range of β-alkenyl-β-hydroxy-N-acyloxazolidin-2-ones results in formation of triols that undergo spontaneous intramolecular 5-exo-trig cyclization reactions to provide hydroxy-γ-butyrolactones. The stereochemistry of these hydroxy-γ-butyrolactones has been established using NOE spectroscopy, which revealed that 1-substituted, 1,1-disubstituted, (E)-1,2-disubstituted, (Z)-1,2-disubstituted, and 1,1,2-trisubstituted alkenes undergo dihydroxylation with anti-diastereoselectivity, while 1,2,2-trisubstituted systems afford syn-diastereoisomers. The synthetic utility of this methodology has been demonstrated for the asymmetric synthesis of the natural product 2-deoxy-d-ribonolactone. Published 2011 by the American Chemical Society.

A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

Enantioselective preparation of P-chiral phosphine oxides

A highly efficient chiral auxiliary-based strategy for the asymmetric synthesis of P-chiral phosphine oxides in >98:2 er has been developed. The methodology involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides.