167102-62-7

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-BOC-4-(METHOXYMETHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE is used as a building block for the synthesis of bioactive molecules, contributing to the development of new drugs and pharmaceutical agents. Its unique chemical properties and the BOC protecting group enable selective reactions and functional group manipulation, facilitating the creation of complex molecular structures with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, (R)-3-BOC-4-(METHOXYMETHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE serves as a valuable precursor for the synthesis of various organic compounds. Its versatility in organic synthesis allows researchers to explore new chemical reactions and develop innovative synthetic pathways, further expanding the scope of chemical knowledge and applications.

InChI:InChI=1/C13H24N2O5/c1-12(2,3)20-11(17)15-9(8-19-13(15,4)5)10(16)14(6)18-7/h9H,8H2,1-7H3/t9-/m1/s1

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 167102-61-6 tert-butyl N-[(1R)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 67-64-1 acetone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 660852-86-8 (4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 

Downstream Products

• 488835-95-6 (4R)-4-(4-benzyloxyphenyl)-3-tert-butoxycarbonyl-2,2-dimethyloxazolidine 
• 1443753-93-2 (3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate 
• 1443753-94-3 C₁₈H₂₅NO₆ 
• 433711-87-6 (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(2,4-dimethoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester 
• 433711-89-8 {(2S)-methoxy-(1R)-[1-(2,4-dimethoxy)-benzyl-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester 
• 433711-82-1 (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid tert-butyl ester 
• 433711-81-0 (5R)-tert-butoxycarbonylamino-(4R)-[hydroxy-(4-methoxybenzyl)-amino]-(6S)-methoxy-(6S)-methylnon-2-ynoic acid ethyl ester 
• 433711-83-2 {(2S)-methoxy-(1R)-[1-(4-methoxybenzyl)-5-oxo-(3S)-Z-propenylpyrrolidin-(2R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester 
• 433711-88-7 {(2S)-methoxy-(1R)-[1'-(2,4-dimethoxybenzyl)-5'-oxo-2',5'-dihydro-1H-pyrrol-(2'R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester 
• 433711-86-5 C₂₂H₃₆N₂O₆ 
• 335693-89-5 {(2S)-methoxy-(1R)-[1'-(4-methoxybenzyl)-5'-oxo-2',5'-dihydro-1H-pyrrol-(2'R)-yl]-(2S)-methylpentyl}-carbamic acid tert-butyl ester 
• 335693-80-6 C₂₁H₃₄N₂O₅ 
• 167102-63-8 (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 

Relevant academic research and scientific papers

Enantiospecific and diastereoselective synthesis of 4,4-disubstituted-3- amino-2-azetidinones, starting from D-serine

A strategy for the preparation of 4,4-disubstituted-3-amino-2- azetidinones, which are useful intermediates for the synthesis of analogues of monosulfactam Tigemonam, was developed. It employs D-serine as chiral starting material and involves, as key steps, the diastereoselective addition of organometal compounds to ketones 9 and the stereospecific cyclization of tertiary alcohols 7 to the β-lactams 6.

A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation

The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.

STABLE N-((1R,2R)-1-(2,3-DIHYDROBENZO[B][1,4]DIOXIN-6-YL)-1-HYDROXY-3-(PYRROLIDIN-1-YL)PROPAN-2-YL) OCTANAMIDE (2R,3R)-2,3-DIHYDROXYSUCCINATE PREMIX AND PROCESS FOR PREPARATION THEREOF

The present invention related to stable N-((1R, 2R)-1-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)- 1-hydroxy-3- (pyrrolidin-1-yl)propan-2-yl) octanamide (2R,3R)- 2,3-dihydroxysuccinate premix of formula (Ia) and its process for preparation thereof. The present invention also related to process for the preparation of N-((1R, 2R)-1-(2,3-dihydrobenzo[b][1,4] dioxin-6- yl)-1-hydroxy-3- (pyrrolidin-1-yl) propan-2-yl) octanamide of formula (I) and pharmaceutically acceptable salts.

DEUTERATED O-SULFATED BETA-LACTAM HYDROXAMIC ACIDS AND DEUTERATED N-SULFATED BETA-LACTAMS

Provided herein are deuterated O-sulfated beta-lactam hydroxamic acids and deuterated N-sulfated beta-lactams, pharmaceutical compositions thereof and methods of treating infectious disease with deuterated compounds or pharmaceutical compositions thereof.

Novel Easily Recyclable Bifunctional Phosphonic Acid Carrying Tripeptides for the Stereoselective Michael Addition of Aldehydes with Nitroalkenes

A novel bifunctional organocatalyst library combining both aminocatalysis and phosphonic acid activation was used for the first time as an efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes with good selectivities up to 95:5 dr and 93:7 er. Due to their high water solubility, the catalysts were easily recyclable and could be reused over several cycles without any significant loss of selectivity.

Reactions of carbon nucleophiles with 2,2,3-trisubstituted ethynylaziridines

Carbon nucleophiles were used to open a 2,2,3-trisubstituted ethynylaziridine. A cyanide nucleophile opened the ring at the more substituted carbon, proceeding regioselectively with inversion of configuration. In an attempt to expand upon the scope of the reaction, Normant cuprates were reacted with a 2,2,3-trisubstituted ethynylaziridine. This reaction produced chiral allenes via an anti-SN2′ pathway. X-ray analysis of a derivative allowed the absolute stereochemistry of the anti-allenes to be assigned as P.

Effects on polo-like kinase 1 polo-box domain binding affinities of peptides incurred by structural variation at the phosphoamino acid position

Protein-protein interactions (PPIs) mediated by the polo-box domain (PBD) of polo-like kinase 1 (Plk1) serve important roles in cell proliferation. Critical elements in the high affinity recognition of peptides and proteins by PBD are derived from pThr/pS

Synthetic studies on callipeltins: Stereoselective syntheses of (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and fmoc-D-allothreonine from serine derivatives

The non-proteinogenic amino acids contained in callipeltins, (3S, 4R)-3, 4-dimefhyl-L-pyroglutamic acid and D-allothreonine, were synthesized from D- or L-serine. The stereoselective synthesis of two methyl groups of (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid was accomplished by diastereoselective hydrogenation and alkylation. Kinetic epimerization of the C-4 methyl substituent followed by Boc-deprotection with 10% TFA gave the desired (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid as a single isomer.

Evolution of the total syntheses of ustiloxin natural products and their analogues

Ustiloxins A-F are antimitotic heterodetic cyclopeptides containing a 13-membered cyclic core structure with a synthetically challenging chiral tertiary alkyl-aryl ether linkage. The first total synthesis of ustiloxin D was achieved in 31 linear steps using an SNAr reaction. An NOE study of this synthetic product showed that ustiloxin D existed as a single atropisomer. Subsequently, highly concise and convergent syntheses of ustiloxins D and F were developed by utilizing a newly discovered ethynyl aziridine ring-opening reaction in a longest linear sequence of 15 steps. The approach was further optimized to achieve a better macrolactamization strategy. Ustiloxins D, F, and eight analogues (14-MeO-ustiloxin D, four analogues with different amino acid residues at the C-6 position, and three (9R,10S)-epi-ustiloxin analogues) were prepared via the second-generation route. Evaluation of these compounds as inhibitors of tubulin polymerization demonstrated that variation at the C-6 position is tolerated to a certain extent. In contrast, the S configuration of the C-9 methylamino group and a free phenolic hydroxyl group are essential for inhibition of tubulin polymerization.

Inhibitors of neuraminidases

Disclosed are compounds of the formula: which are useful for inhibiting neuraminidases from disease-causing microorganisms, especially, influenza neuraminidase. Also disclosed are compositions and methods for preventing and treating diseases caused by mic