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1-(t-butyldimethylsilyloxy) Benzotriazole (TBDMS-OBt): A New And Novel Reagent For The Synthesis Of Peptides

S. Tantry, V. V. S. Babu
Published 2006 · Chemistry

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Synthesis and use of 1-(t-butyldimethylsilyloxy)benzotriazole (TBDMS-OBt) in the coupling of Fmoc-amino acid chlorides to amino free amino acid esters in homogeneous solution phase is described. The coupling required no addition of base and was fast and racemization free. Work up and isolation of products were easy. Yield, purity and1H NMR analysis of peptides, synthesised by this method, were satisfactory.
This paper references
10.1021/JO0017640
One-carbon homologation of carboxylic acids via BtCH(2)TMS: a safe alternative to the Arndt--Eistert reaction.
A. Katritzky (2001)
10.1021/JO00239A037
Methyl ester nonequivalence in the 1H NMR spectra of diastereomeric dipeptide esters incorporating N-terminal .alpha.-phenylglycine units
L. A. Carpino (1988)
10.1021/JO00008A012
[(9-Fluorenylmethyl)oxy]carbonyl (Fmoc) amino acid chlorides in solid-phase peptide synthesis
L. A. Carpino (1991)
10.1016/S0040-4039(97)00336-5
Synthesis of microcolin analogs using trimethylsilylated lactams
Ralph-Heiko Mattern (1997)
10.1039/B006756N
(Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid azides: Synthesis, isolation, characterisation, stability and application to synthesis of peptides
V. V. S. Babu (2000)
10.1016/S0040-4039(98)02169-8
SYNTHESIS OF PEPTIDES EMPLOYING FMOC-AMINO ACID CHLORIDES AND COMMERCIAL ZINC DUST
H. Gopi (1998)
10.1002/CHIN.199139225
((9‐Fluorenylmethyl)oxy)carbonyl Amino Acid Chlorides in Solid‐Phase Peptide Synthesis.
L. A. Carpino (1991)
Recently 1-(trimethylsilylmethyl) benzotriazole was used in homologation of carboxylic acids as a safe alternative to the Arndt-Eistert reaction by
R Katritzky (2001)
10.1021/JO00369A042
(Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and application to the rapid synthesis of short peptide segments
L. A. Carpino (1986)
10.1080/00304940109356592
NEW TRENDS IN PEPTIDE COUPLING REAGENTS
Fernando Albeiicio (2001)
10.1016/S0040-4039(96)01507-9
Incorporation of Cα-methyl amino acids by solid phase peptide synthesis in a peptide sequence
A. Brunissen (1996)
10.1111/J.1399-3011.1994.TB00400.X
Synthesis of peptides mediated by KOBt.
K. M. Sivanandaiah (1994)
10.1039/A700731K
Convenient and stereospecific homologation ofN-fluorenylmethoxycarbonyl-α-amino acids totheir β-homologues
A. Leggio (1997)
10.1016/S0040-4039(97)10504-4
Protected amino acid chlorides vs protected amino acid fluorides: Reactivity comparisons.
L. A. Carpino (1998)
10.1021/JO980807Y
Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1
F. Albericio (1998)
10.1111/J.1399-3011.1995.TB01051.X
Solid-phase synthesis of oxytocin using iodotrichlorosilane as Boc deprotecting agent.
K. M. Sivanandaiah (1995)
10.1021/JA00772A043
Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives
E. Corey (1972)
10.1111/J.1399-3011.2001.00790.X
Deprotonation of hydrochloride salts of amino acid esters and peptide esters using commercial zinc dust.
K. Ananda (2001)
10.1016/S0040-4039(97)10724-9
Rapid and efficient synthesis of peptide fragments containing α-aminoisobutyric acid using Fmoc-amino acid chlorides/potassium salt of 1-hydroxybenzotriazole
V. V. S. Babu (1998)
Recently 1-(trimethylsilylmethyl) benzotriazole was used in homologation of carboxylic acids as a safe alternative to the Arndt-Eistert reaction
L. A. Carpino (1991)
10.1016/S0040-4039(00)80080-5
Chlorotrimethylsilane-phenol as a mild deprotection reagent for the tert-butyl based protecting groups in peptide synthesis
E. Kaiser (1988)
10.1007/BF02443561
Synthesis of peptides employing Fmoc-/Boc-/Z-amino acid fluorides and activated commercial zinc dust
V. V. S. Babu (2006)
10.1039/C39790000495
Trimethylsilyl iodide as a peptide deblocking agent
Richard S. Lott (1979)
10.1021/AR950023W
Peptide Synthesis via Amino Acid Halides
L. A. Carpino (1996)



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