79069-55-9

Upstream product

• 87694-54-0 N^α-(t-butoxycarbonyl)-O-benzyl-L-Threonine N-methoxy-N-methylamide 
• 79069-63-9 tert-butyl [(2R,3R)-3-(benzyloxy)-1-hydroxybutan-2-yl]carbamate 
• 84890-92-6 C₂₁H₃₁NO₇ 
• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 15260-10-3 N-(t-Butyloxycarbonyl)-O-(phenylmethyl)-L-threonine 
• 87694-54-0 tert-butyl ((2S,3R)-3-(benzyloxy)-1-(methoxy(methyl)amino)-1-oxobutan-2-yl)carbamate 

Downstream Products

• 228868-10-8 ((2R,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butylamino)-acetic acid methyl ester 
• 1304048-96-1 C₁₅H₂₀INO₃ 
• 1304048-92-7 C₂₂H₂₈INO₄ 
• 1304048-99-4 tert-butyl [(Z)-1-(3-iodophenyl)-1-oxobut-2-en-2-yl]carbamate 
• 1304048-93-8 tert-butyl [(2S,3R)-3-(benzyloxy)-1-(3-iodophenyl)-1-oxobutan-2-yl]carbamate 
• 1391707-52-0 C₁₇H₂₇NO₄ 
• 1265146-07-3 C₂₂H₃₄N₂O₆ 
• 1265146-06-2 C₂₉H₄₂N₂O₇ 
• 1265145-95-6 C₂₉H₄₄N₂O₈ 
• 769963-66-8 N-{(S)-1-[(1R,2R)-2-Benzyloxy-1-(5-fluoro-2,3-dihydro-indol-1-ylmethyl)-propylcarbamoyl]-3-cyclohexyl-propyl}-3-methoxy-benzamide 
• 879219-19-9 [(1R,2R)-2-Benzyloxy-1-(5-fluoro-2,3-dihydro-indol-1-ylmethyl)-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of threo-β-aminoalcohols from aminoaldehydes via chelation-controlled additions. Total synthesis of l-threo sphingosine and safingol

Chelation-controlled addition of organocuprates to N-carbamoyl aminoaldehydes, prepared from functionalized amino acids, generated predominately the threo-β-amino alcohol derivatives through chelation with the carbamoyl moiety. The carbamate group is a stronger chelating group than other potentially good chelators, for example ethers, esters, thioethers, and gives good diastereoselectivity with cuprates. Thus addition of lithium divinylcuprate to the aldehyde generated from the serine derivative 25 in the presence of extra copper for chelation afforded the threo compound 26 in 83% yield. Cross-metathesis and cleavage of the protecting groups furnished l-threo sphingosine 21. In addition the lyso-sphingolipid protein kinase C inhibitor, safingol, 22, was prepared from commercially available O-benzyl N-BOC serine 28 in six steps and 56% overall yield by this method.

Pyrrole-based scaffolds for turn mimics

Two amino acid derived synthons were combined to give homopropargylic amines 2. Platinum dichloride was used to cyclize these intermediates into pyrroles 3 which collapsed to the target secondary structure mimics 1 on treatment with base. Side chains of these compounds overlay with an idealized type 1 β-turn and with an inverse γ-turn.(Figure Presented)

Expedient synthesis of 1,3-substituted benzene peptidomimetics

A synthetic route for replacing the central amino acid in the tripeptide Thr-Ala-Val (TAV) with a 1,3-substituted benzene ring was developed. l-Threonine was introduced into the benzene ring by a Grignard reaction with protected l-threoninal, where the na

Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: Optimization of P1 and N-aryl

A systematic study of anilines led to the discovery of a metabolically robust fluoroindoline replacement for the alkoxy aniline toxicophore in 1. Investigations of the P1 pocket resulted in the discovery of a wide tolerance of functionality leading to the discovery of 11 as a potent and selective inhibitor of cathepsin S.

Synthesis of new chiral peptide nucleic acid (PNA) monomers by a simplified reductive amination method

The aim of this work was the preparation of four new peptide nucleic acid (PNA) monomer backbone by reductive amination of N(α)-Boc-protected chiral amino aldehydes, derived from Leu, Phe, Tyr(Bzl), and Thr(Bzl), with methyl glycinate. To the crude 2-subs