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Literature DB >> 18092797

Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids.

Buddy Soto-Cairoli¹, Jorge Justo de Pomar, John A Soderquist.

Abstract

The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that < or =2% racemization occurs in the 1 --> 8 conversions.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 18092797 PMCID： PMC2563420 DOI： 10.1021/ol7028993

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

12 in total

Review 1. Protease inhibitors: current status and future prospects.

Authors: D Leung; G Abbenante; D P Fairlie
Journal: J Med Chem Date: 2000-02-10 Impact factor: 7.446

2. Synthesis and diastereoselective reactions of n,n-dibenzylamino aldehydes and related compounds.

Authors: M T Reetz
Journal: Chem Rev Date: 1999-05-12 Impact factor: 60.622

Review 3. Irreversible inhibitors of serine, cysteine, and threonine proteases.

Authors: James C Powers; Juliana L Asgian; Ozlem Dogan Ekici; Karen Ellis James
Journal: Chem Rev Date: 2002-12 Impact factor: 60.622

4. Control of helix formation in vinylogous gamma-peptides by (E)- and (Z)-double bonds: a way to ion channels and monomolecular nanotubes.

Authors: Carsten Baldauf; Robert Günther; Hans-Jörg Hofmann
Journal: J Org Chem Date: 2005-07-08 Impact factor: 4.354

5. Reduction of silyl esters of amino acids.

Authors: P S Venkateswaran; T J Bardos
Journal: J Org Chem Date: 1967-04 Impact factor: 4.354

6. Trimethylsilylation of amino acids derivatization and chromatography.

Authors: C W Gehrke; K Leimer
Journal: J Chromatogr Date: 1971-05-06

7. E-olefin dipeptide isostere incorporation into a polypeptide backbone enables hydrogen bond perturbation: probing the requirements for Alzheimer's amyloidogenesis.

Authors: Yanwen Fu; Jan Bieschke; Jeffery W Kelly
Journal: J Am Chem Soc Date: 2005-11-09 Impact factor: 15.419

2. DIBALH: from known fundamental to an unusual reaction; chemoselective partial reduction of tertiary amides in the presence of esters.

Authors: Yu Jin Heo; Hyun Tae Kim; Ashok Kumar Jaladi; Duk Keun An
Journal: RSC Adv Date: 2021-10-18 Impact factor: 3.361

2 in total

Enantiomerically pure alpha-amino aldehydes from silylated alpha-amino acids.

Review 1. Protease inhibitors: current status and future prospects.

2. Synthesis and diastereoselective reactions of n,n-dibenzylamino aldehydes and related compounds.

Review 3. Irreversible inhibitors of serine, cysteine, and threonine proteases.

4. Control of helix formation in vinylogous gamma-peptides by (E)- and (Z)-double bonds: a way to ion channels and monomolecular nanotubes.

5. Reduction of silyl esters of amino acids.

6. Trimethylsilylation of amino acids derivatization and chromatography.

7. E-olefin dipeptide isostere incorporation into a polypeptide backbone enables hydrogen bond perturbation: probing the requirements for Alzheimer's amyloidogenesis.

8. Synthesis of (-)-quinocarcin by directed condensation of alpha-amino aldehydes.

9. Synthetic enantiopure aziridinomitosenes: preparation, reactivity, and DNA alkylation studies.

10. alpha-aminoaldehydes: transition state analogue inhibitors of leucine aminopeptidase.

1. Characteristic conformation of Mosher's amide elucidated using the cambridge structural database.

2. DIBALH: from known fundamental to an unusual reaction; chemoselective partial reduction of tertiary amides in the presence of esters.