115186-34-0

Upstream product

• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 

Downstream Products

• 1381872-59-8 C₂₂H₂₇NO₄ 
• 229644-35-3 [(S)-1-((S)-1-Benzyloxymethyl-2-oxo-4-phenyl-butylcarbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 229644-32-0 [1-(4-benzyloxymethyl-5-phenethyl-thiazol-2-yl)-propyl]-carbamic acid tert-butyl ester 
• 497830-77-0 (3R,3aR,4S,7aR)-2-Benzyl-3-benzyloxymethyl-1-oxo-6-phenyl-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester 
• 497830-88-3 (E)-(R)-4-[Benzyl-((E)-4-oxo-4-phenyl-but-2-enoyl)-amino]-5-benzyloxy-pent-2-enoic acid ethyl ester 
• 497830-76-9 (3R,3aR,4S,7aR)-2-Benzyl-3-benzyloxymethyl-6-methyl-1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester 
• 497830-86-1 (E)-(R)-4-[Benzyl-((E)-4-oxo-pent-2-enoyl)-amino]-5-benzyloxy-pent-2-enoic acid ethyl ester 
• 497830-97-4 (E)-(R)-4-Benzylamino-5-benzyloxy-pent-2-enoic acid ethyl ester 
• 497831-01-3 ethyl (R,E)-5-(benzyloxy)-4-((tert-butoxycarbonyl)amino)pent-2-enoate 
• 1006036-05-0 (S)-(+)-trans-5-benzyloxy-4-amino-2-pentenoic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of new chiral peptide nucleic acid (PNA) monomers

We have synthesised a series of new chiral type I peptide nucleic acid monomers in total yields of 36-53%, derived from Val, Ile, Ser(Bzl), Pro, and Trp, employing convenient procedure.

Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Br?nsted Bases

The high tendency of α-amino aldehydes to undergo 1,2-additions and their relatively low stability under basic conditions have largely prevented their use as pronucleophiles in the realm of asymmetric catalysis, particularly for the production of quaternary α-amino aldehydes. Herein, it is demonstrated that the chemistry of α-amino aldehydes may be expanded beyond these limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produces densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling leads to the proposal that intramolecular hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde is key for reaction stereocontrol.

Gold-catalyzed synthesis of enantioenriched furfurylamines from amino acids

Abstract A convenient gold-catalyzed asymmetric synthesis of polysubstituted furfurylamines starting from amino acids has been achieved. The cyclization proceeded under mild conditions and generally provided the furan or iodofuran derivatives in good to e

Novel branched isocyanides as useful building blocks in the Passerini-amine deprotection-acyl migration (PADAM) synthesis of potential HIV-1 protease inhibitors

Novel branched isocyanides have been prepared from l-serine and used as building blocks in the Passerini-amine deprotection-acyl migration (PADAM) sequence for the preparation of compounds with activity against HIV-1 protease.

A simple γ-backbone modification preorganizes peptide nucleic acid into a helical structure

Peptide nucleic acid (PNA) is a synthetic analogue of DNA and RNA, developed more than a decade ago in which the naturally occurring sugar phosphate backbone has been replaced by the N-(2-aminoethyl) glycine units. Unlike DNA or RNA in the unhybridized st

ALKENE MIMICS

Ac-Phe-Tyr-phosphoSer-Ψ[CH=C]-Pro-Arg-NH2AND Fmoc-bis(pivaloylmethoxy)phosphoSer-Ψ[CH=C]-Pro-2-aminoethyl-(3-indole); and their Phospho-(D)-serine stereoisomers are novel compounds. Ψ refers to a pseudo amide. Such novel compounds advantageousl

Serine-cis-proline and serine-trans-proline isosteres: Stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements

Two new amide isosteres of Ser-cis-Pro and Ser-trans-Pro dipeptides were designed and stereo-selectively synthesized to be incorporated into potential inhibitors of the phosphorylation-dependent peptidylprolyl isomerase Pin1, an essential regulator of the

A practical approach to the synthesis of 2,4-disubstituted oxazoles from amino acids

(Matrix presented) A new sequence for the synthesis of various 2,4-disubstituted oxazoles from α-amino acids is reported. The method is shown to be general and incorporates the reagent combination, triphenylphosphine/hexachloroethane, for cyclodehydration of intermediate α-acylamino aldehydes. Implementation of this reagent system for the conversion of α-acylamino ketones to oxazoles is briefly investigated.

Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels-Alder reaction

Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized

Solvent-dependent stereoselectivity in a Still-Wittig rearrangement: An experimental and ab initio study

(formula presented) The Still-Wittig rearrangement gave opposite selectivities for (Z:E)-alkenes in THF (3:1) vs toluene (1:3) in the synthesis of serine-proline dipeptide amide isosteres. Four transition states leading to (Z)-and (E)-alkenes with THF and