329327-45-9

Basic information

• Product Name: Boc-(L-Oxd)3-OBn
• Synonyms: Boc-(L-Oxd)3-OBn
• CAS NO: 329327-45-9
• Molecular Weight: 589.556
• Mol File: 329327-45-9.mol

Chemical Properties

• CAS DataBase Reference: Boc-(L-Oxd)3-OBn(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-(L-Oxd)3-OBn(329327-45-9)
• EPA Substance Registry System: Boc-(L-Oxd)3-OBn(329327-45-9)

Safety Data

• Hazardous Substances Data: 329327-45-9(Hazardous Substances Data)

Upstream product

• 171563-10-3 benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate 
• 329327-44-8 Boc-(L-Oxd)2-OPfp 
• 329327-37-9 (4S,5R)-N-Boc-4-carboxybenzyl-5-methyloxazolidin-2-one 
• 329327-36-8 (2S,3R)-N-Boc-2-carboxybenzyl-3-methylaziridine 
• 329327-38-0 (4S,5R)-N-Boc-4-carboxy-5-methyloxazolidin-2-one 
• 163188-28-1 benzyl N-Boc-(3R)-aminobutanoate 
• 329327-40-4 Boc-(L-Oxd)2-OBn 
• 329327-39-1 Boc-L-Oxd-OPfp 
• 329327-43-7 Boc-(L-Oxd)2-OH 

Downstream Products

• 523992-87-2 Boc-(L-Oxd)4-OPfp 
• 523992-89-4 Boc-(L-Oxd)5-OBn 
• 523992-82-7 Boc-(L-Oxd)3-OPfd 
• 329327-46-0 Boc-(L-Oxd)4-OBn 

Relevant articles and documents

Pseudopeptide foldamers - The homo-oligomers of benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate

A 2-oxo-1,3-oxazolidine-4-carboxylic acid was designed as a new, conformationally restricted building block for the construction of pseudopeptide foldamers. IR, 1H NMR and CD techniques, implemented by detailed DFT computational modeling, were

Synthesis of oligomers of trans-(4S,5R)-4-carboxybenzyl 5-methyl oxazolidin-2-one: An approach to new foldamers

The synthesis of two oligomers containing three and four residues, respectively, of trans-(4S,5R)-4-carboxy 5-methyloxazolidin-2-ones is described. The monomer is obtained by starting from benzyl-N-Boc-(3R)-aminobutanoate, by cyclization into the corresponding trans-(2S,3R)-2-carboxybenzyl-3-methyl-N-Boc-aziridine and rearrangement of the product to trans-(4S,5R)-4-carboxybenzyl-5-methyloxazolidin-2-one, catalyzed by Sn(OTf)2. The oligomers are synthesized by activating the carboxy group as its pentaflourophenyl ester. The trimer and the tetramer are obtained in good yield, and their 1H NMR spectra suggest that these molecules fold in ordered structures, where the C-4 hydrogen of a ring is always close to the carbonyl of the next ring. This result shows that the 4-carboxy-5-substituted-oxazolidin-2-ones are a new class of pseudoprolines which fully control the formation of a Xaai-1-Proi peptide bond in the trans conformation and are complementary to the pseudoprolines obtained from cyclocondensation of cysteine, serine, or threonine and aldehydes or ketones, which strongly favor the Xaai-1-Proi peptide bond in the cis conformation.