95599-23-8

Upstream product

• 196862-32-5 methyl (2S,3R)-2-(benzylamino)-3-hydroxybutanoate 
• 40216-78-2 (2S,3R)-3-Hydroxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid methyl ester 
• 3373-59-9 L-threonine methyl ester 
• 197146-85-3 N-benzyl-N-methyl-L-threonine methyl ester 
• 368424-95-7 methyl (4S,5R)-5-methyloxazolidine-4-carboxylate 

Downstream Products

• 197146-87-5 (4R,5S)-5-{(S)-1-[((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propyl)-methyl-carbamoyl]-ethyl}-4-methyl-2-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Preparation of the optically pure N-methyl amino ester method and product

The invention belongs to the field of organic synthesis of amino acids and discloses a method for preparing optically pure N-methyl amino-acid ester. The method comprises the following steps of carrying out esterification reaction on amino acid as a starting raw material and aldehyde to form an imine intermediate, carrying out reductive amination in the presence of palladium carbon, and carrying out hydrogenation and debenzylation to finally synthesize optically pure N-methyl amino-acid ester. The method has the advantages of simplicity in method, mild reaction conditions and good adaptability and side chains of D-type or L-type amino acid do not need to be protected.

Facile synthesis of highly functionalized N-methyl amino acid esters without side-chain protection

(Chemical Equation Presented) The facile, two-pot synthesis of N-methyl amino acid esters by way of reductive amination is presented. Side chain protection schemes are not required, the starting materials are all commercially available, and the synthetic

Stereoelectronic control of oxazolidine ring-opening: Structural and chemical evidences

Ring opening of oxazolidines derived from tris(hydroxymethyl)aminomethane, L-serine and L-threonine was investigated. It was shown that n(N)→σ*(C-O) electron delocalization (endo-anomeric effect) occurring in the five-membered ring plays a major role in the cleavage of the intracyclic C-O bond. The present work establishes that when the nitrogen lone pair is conjugated with a carbonyl group (n(N)→π(C=O) delocalization) as happens in N-acyloxazolidines, both hydrolysis and reductive ring-opening become much more difficult as a consequence of a concomitant decrease of oxygen basicity and of an increase of the intracyclic C-O bond strength.

Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea

The novel cyclic depsipeptides papuamides A (1), B (2), C (3), and D (4) have been isolated from Papua New Guinea collections of the sponges Theonella mirabilis and Theonella swinhoei. Their structures were determined by a combination of spectroscopic analysis and chemical degradation and derivatization studies. In addition to glycine, alanine, and threonine, these peptides contain a number of unusual amino acids including 3,4- dimethylglutamine, β-methoxytyrosine, 3-methoxyalanine, and 2,3- diaminobutanoic acid or 2-amino-2-butenoic acid residues. Papuamides A-D (1- 4) are also the first marine-derived peptides reported to contain 3- hydroxyleucine and homoproline residues. These peptides also contain a previously undescribed 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid moiety N-linked to a terminal glycine residue. Papuamides A (1) and B (2) inhibited the infection of human T-lymphoblastoid cells by HIV-1(RF) in vitro with an EC50 of approximately 4 ng/mL. Compound 1 was also cytotoxic against a panel of human cancer cell lines with a mean IC50 of 75 ng/mL.

N-methyl threonine analogues of deglycobleomycin A2: Synthesis and evaluation

The synthesis of 5 and its D-allo-threonine epimer 6 and the comparison of their DNA cleavage efficiency and selectivity with that of deglycobleomycin A2 (3) are detailed. The studies illustrate that N-methylation of the L-threonine subunit wit

Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters

A novel method for the synthesis of N-methylserines has been developed.The oxazolidines 4 are formed by condensation of the serine methyl esters 1 with formaldehyde.These intermediates are subsequently reduced to the N-methylserine methyl esters 9 by an acid-catalyzed ring opening via their iminium ions 2 with triethylsilane/trifluoroacetic acid. key words: Serine derivatives; bislactim ether method.