117833-92-8

Basic information

• Product Name: (S)-BENZYL 4-FORMYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE
• Synonyms: (S)-BENZYL 4-FORMYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE
• CAS NO: 117833-92-8
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.29
• Mol File: 117833-92-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-BENZYL 4-FORMYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-BENZYL 4-FORMYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE(117833-92-8)
• EPA Substance Registry System: (S)-BENZYL 4-FORMYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE(117833-92-8)

Safety Data

• Hazardous Substances Data: 117833-92-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate is used as an intermediate in organic synthesis for the production of pharmaceuticals. Its unique structure and properties contribute to the development of new drugs, offering potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-Benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate is also utilized as an intermediate in organic synthesis. Its role in the production of various agrochemicals highlights its versatility and importance in this sector.
Used in Organic Synthesis:
(S)-Benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate serves as a building block in the synthesis of a wide range of organic compounds. Its unique structure allows for the creation of diverse molecules with potential applications in various industries.

Upstream product

• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 684270-34-6 benzyl N-[(1S)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate 
• 501-53-1 benzyl chloroformate 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 412917-35-2 benzyl (4S)-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 117833-99-5 N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine 

Downstream Products

• 321658-31-5 (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-2-carbomethoxyvinyl>oxazolidine 
• 239789-45-8 benzyl (R)-2,2-dimethyl-4-(2-aza-4-tert-butoxycarbonylamino)butyl-1,3-oxazolidine-3-carboxylate 
• 213454-11-6 (S)-4-[(E)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 505086-79-3 (R,R)-4-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-yl)(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 497084-57-8 N-benzyloxycarbonyl-4(R)-[3'-oxo-(1'E)-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine 
• 444687-22-3 (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 271260-90-3 benzyl (4R)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate 
• 412917-47-6 benzyl (4S)-4-[(E)-2-iodoethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 420107-61-5 (S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 420107-71-7 (S)-4-[(S)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 213696-73-2 (R)-2,2-dimethyl-3-benzyloxycarbonyl-4-(2,2-dibromoethenyl)-oxazolidine 
• 133625-95-3 (E)-(R)-N-Cbz-2,2-dimethyl-4-(2-carboxyethenyl)oxazolidine methyl ester 
• 145625-10-1 3-carbobenzoxy-2,2-dimethyl (R)-4-oxazazolidine aldoxime 
• 117833-94-0 (Z)-(R)-N-Cbz-2,2-dimethyl-4-(5-cyano-1-pentenyl)oxazolidine 

Relevant articles and documents

Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

Diastereocontrolled multicomponent pathway to 3,4-heterocycle-annulated tetrahydro-β-carbolines

A diastereoselective synthesis, using the Yonemitsu-type trimolecular condensation as the key step, has been used for the preparation of 3,4-heterocycle(furanone-, pyrrolidinone- and pyranone-) annulated tetrahydro-β-carbolines. The chirality of D-gly-cer

Synthesis and growth inhibitory activity of chiral 5-hydroxy-2-N-acyl-(3E)-sphingenines: Ceramides with an unusual sphingoid backbone

The unusual sphingoid base 5-hydroxy-3-sphingenine was identified in the hydrolysate of brain sphingolipids more than 40 years ago. We present here the first synthesis of the 5R and 5S diastereoisomers of the N-acyl derivatives of 5-hydroxy-3-sphingenine, 2 and 3, respectively, which represent regioisomers of (2S,3R)-ceramide (1). The key steps include the synthesis of a,β-unsaturated ketone intermediates 4 and 5 from N-Cbz- and N-Boc -L-serine and diastereoselective reduction of the enones. The configuration at the new carbinol center was deduced by proton NMR analysis of (R)- and (S)-Mosher [methoxy(trifluoromethyl)phenylacetate] ester derivatives. Ceramide analogues 2 and 3 showed a markedly higher antiproliferative activity than 1 on MCF-7 cells.

Homochiral 4-azalysine building blocks: Syntheses and applications in solid-phase chemistry

Anomalous amino acids not only play central roles as mimics of natural amino acids but also offer opportunities as unique building blocks for combinatorial chemistry. This paper describes the chiral syntheses and solid-phase applications of a versatile atypical amino acid, 4-azalysine (2,6-diamino-4-azahexanoic acid) 1. The syntheses of differentially protected 4-azalysine derivatives 28a-e have been developed by two efficient and inexpensive routes that start either from Garner's aldehyde 16 or the chiron (S)-Nα-Cbz-2,3-diaminopropionic acid 23. Both approaches employ the convergent modular concept and exploit reductive amination of aldehydes with amines as the key step for the fusion of the two segments. In the first route, the overall process inverts the chirality of the starting material, L-serine, and thus provides an excellent route to the unnatural D-isomers. The alternative route starting from L-asparagine provides a shorter and high-yielding route to orthogonally protected 4-azalysine derivatives. The corresponding N2-Fmoc-4-azalysines 31a-e, readily derived from the key intermediate 27, are compatible with the Fmoc-based solid-phase peptide synthesis (SPPS) and solid-phase organic chemistry (SPOC) protocols. Furthermore, the utility and versatility of another key structure, tris-Boc-4-azalysine 2 in the engineering of novel high-loading dendrimeric polystyrene resins 33 and 36, have been demonstrated. Following derivatization with the Rink amide linker 34, the stability and robustness of these resin-bound dendrimers 35 and 37 in the synthesis of small molecules using a range of reaction conditions (e.g., Mitsunobu and Suzuki reactions) have been effectively illustrated.

Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

A synthetic azinomycin analogue with demonstrated DNA cross-linking activity: Insights into the mechanism of action of this class of antitumor agent

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Stereoselective synthesis of differentially protected derivatives of the higher amino sugars destomic acid and lincosamine from serine and threonine

The aminoheptose destomic acid (3.5) and the aminooctose lincosamine (6.8) were synthesized in protected form by parallel sequences starting from the oxazolidine derivatives 2.4 and 5.1 of N-CBz serinal and N-BOC threoninal. The parallel sequences feature

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New Synthetic Methodology for the Synthesis of 7-Substituted Tetrahydroazepin-2-ones

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