90719-32-7 Usage
Description
(S)-4-Benzyl-2-oxazolidinone is a chiral compound featuring a benzyl group attached to a five-membered oxazolidinone ring. It is an important building block in organic synthesis and has unique stereochemical properties due to its (S)-configuration.
Uses
Used in Pharmaceutical Industry:
(S)-4-Benzyl-2-oxazolidinone is used as a chiral auxiliary in asymmetric alkylation reactions for the synthesis of various pharmaceutical compounds. Its ability to induce stereoselectivity in these reactions makes it a valuable tool in the development of enantiomerically pure drugs.
Used in Organic Synthesis:
(S)-4-Benzyl-2-oxazolidinone is used as a chiral building block in the synthesis of complex organic molecules, such as natural products and bioactive compounds. Its unique structure allows for the creation of new chiral centers and the formation of diverse molecular frameworks.
Used in Chiral Auxiliary Asymmetric Synthesis:
(S)-4-Benzyl-2-oxazolidinone is used as a chiral auxiliary in asymmetric synthesis, providing a stereochemical advantage in the formation of new chiral centers. This application is particularly useful in the synthesis of enantiomerically pure compounds, which are often required for biological activity and pharmaceutical applications.
Used in the Synthesis of (S)-Equol:
(S)-4-Benzyl-2-oxazolidinone has been specifically used in the synthesis of (S)-equol, a bioactive compound with potential health benefits. Its role in this synthesis highlights its utility in the preparation of biologically relevant molecules.
Used in Preparation and Functionalization of Chiral, Stabilized Ylides:
(S)-4-Benzyl-2-oxazolidinone is used in the preparation and functionalization of chiral, stabilized ylides. These ylides are valuable intermediates in organic synthesis, and the chiral nature of the oxazolidinone ring can impart selectivity in subsequent reactions.
Used in Asymmetric Synthesis of (3R)and (3S)-Piperazic Acid:
(S)-4-Benzyl-2-oxazolidinone has been employed in the asymmetric synthesis of (3R)and (3S)-piperazic acid, which are important chiral building blocks in the pharmaceutical industry. Its use in this context further demonstrates its versatility and importance in the synthesis of enantiomerically pure compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 90719-32-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,0,7,1 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 90719-32:
(7*9)+(6*0)+(5*7)+(4*1)+(3*9)+(2*3)+(1*2)=137
137 % 10 = 7
So 90719-32-7 is a valid CAS Registry Number.
90719-32-7Relevant articles and documents
Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides
Bhunia, Subhajit,De, Subhadip,Ma, Dawei
supporting information, (2022/02/09)
N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature. Excellent chemoselectivity reached between
Synthesis of Aminomethylene- gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism
Cheviet, Thomas,Peyrottes, Suzanne
, p. 3107 - 3119 (2021/02/05)
A broad range of N-carbamoylaziridines were obtained and then treated by the diethyl phosphonate anion to afford α-methylene-gem-bisphosphonate aziridines. Study of the reaction's scope and additional experiments indicates that the transformation proceeds via a new mechanism involving the chelation of lithium ion. This last step is crucial for the reaction to occur and disfavors the aziridine ring-opening. A phosphonate-phosphate rearrangement from a α-hydroxybisphosphonate aziridine intermediate is also proposed for the first time. This reaction provides a simple and convenient method for the synthesis of a highly functionalized phosphonylated aziridine motif.
Synthesis of pyrroloindolines through formal [3 + 2]-cycloaddition of indoles with chiral N-2-acetamidoacrylyl oxazolidinones
Smith, Isaac T.,Neeley, Jared B.,Brinley, Tanner D.,Fullmer, Peter R.,Andrus, Merritt B.
supporting information, (2020/05/01)
Chiral N-2-acetamidoacrylyl oxazolidinones were produced and reacted with indoles under Lewis acid conditions to generate hexahydropyrrolo[2,3-b]indole products in a formal [3 + 2] cycloaddition process. Optimal conditions included the use of tin(IV) chloride in methylene chloride at 0 °C. Pyrroloindoline products were obtained from various indoles with shorter reaction times (12 hr) up to 91% yield with high, >20:1 exo selectivity. A mechanism involving reversible conjugate addition followed by an enamine lone-pair-iminium capture, tautomerization, and tin-enolate protonation accounts for the selectivity. The method enables selective applications to pyrroloindoline targets and further refinement with chiral catalysts.