2-Chloro-4,6-dimethoxy-1,3,5-triazine: A New Effective and Convenient Coupling Reagent for Cephalosporin Derivatives

Lee, Hong-Woo; Kang, Tae Won; Hoi, Kyung; Kim, Eung-Nam; Choi, Nam-Hee; Kim, Jung-Woo; Hong, Chung Il

doi:10.1080/00397919808006831

Cited by 19 publications

(3 citation statements)

References 7 publications

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“…In fact, triazine esters 1 have already been found more reactive than any other acylating reagent, including N -hydroxybenzotriazole esters . Moreover, many authors used successfully triazine reagents for the synthesis of peptides, carboxylic acid esters, amides, pholic acid antagonists, β-lactames, carotenoids, fullerenes, and others compounds. , …”

Section: Introductionmentioning

confidence: 99%

N-Triazinylammonium Tetrafluoroborates. A New Generation of Efficient Coupling Reagents Useful for Peptide Synthesis

et al. 2005

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A new generation of triazine-based coupling reagents (TBCRs), designed according to the concept of "superactive esters", was obtained by treatment of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium (DMTMM) chloride with lithium or silver tetrafluoroborate. The structure of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate was confirmed by X-ray diffraction. Activation of carboxylic acids by using this reagent proceeds via triazine "superactive ester". The coupling reagent was successfully used for the synthesis of Z-, Boc-, and Fmoc-protected dipeptides derived from natural and unnatural sterically hindered amino acids and for fragment condensation, in 80-100% yield and with high enantiomeric purity. The manual SPPS of the ACP(65-74) peptide fragment (H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-OH) proceeded significantly faster than with TBTU or HATU, as well as the automated SPPS of the same fragment gave a purer product than by using TBTU or PyBOP. The reagent was also demonstrated to be efficient in on-resin head-to-tail cyclization of constrained cyclopeptides, in SPPS synthesis of Aib peptides, and in the synthesis of esters from appropriate acids, alcohols, and phenols. The high efficiency and versatility of this new generation of TBCRs confirm, for the first time, the usefulness of the concept of "superactive esters" in rational design of the structure of coupling reagents.

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Section: Introductionmentioning

confidence: 99%

N-Triazinylammonium Tetrafluoroborates. A New Generation of Efficient Coupling Reagents Useful for Peptide Synthesis

et al. 2005

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“…2-Chloro-4,6-dimethoxy-1,3,5-triazine has been used as reagent for the synthesis of aldehydes [537], esters [538], amides [539,540] or oxazolines [541] from carboxylic acids; as coupling agents for cephalosporin derivatives [542]; and to separate an enantiomeric mixture of amides or dipeptides [543].…”

Section: Relevant Natural and Useful Compoundsmentioning

confidence: 99%

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Oliva¹,

Laza²,

Ocáriz³

2011

Modern Heterocyclic Chemistry

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“…The concept of active esters and superactive esters as reactive intermediates in acylation reactions has been proven useful for the synthesis of peptides, amides, or α-lactams, and carboxylic acid esters as well as other compounds . Among many activators tested in these reactions, mostly derivatives of N -hydroxybenzotriazoles or azabenzotriazoles have been employed.…”

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confidence: 99%

Chemoselective Activation of Nucleoside 3‘-O-Methylphosphonothioates with 1,3,5-Triazinyl Morpholinium Salts

2007

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Chemoselective and stereospecific O-activation of 2'-deoxynucleoside 3'-O-methylphosphonothioates 5 with N-methyl-N-4,6-dimethoxy-1,3,5-triazin-2-yl morpholinium salts results in formation with retention of configuration of 5'-O-DMT-2'-deoxynucleoside 3'-O-(4,6 dimethoxy-1,3,5-triazin-2-yl methylphosphonothioates (7). Active esters 7 are convenient intermediates for hydrolytic interconversion of RP-5 into SP-5 and can be used as monomers for stereoselective synthesis of dinucleoside (3',5')-methyl phosphonothioates.

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2-Chloro-4,6-dimethoxy-1,3,5-triazine: A New Effective and Convenient Coupling Reagent for Cephalosporin Derivatives

Cited by 19 publications

References 7 publications

N-Triazinylammonium Tetrafluoroborates. A New Generation of Efficient Coupling Reagents Useful for Peptide Synthesis

N-Triazinylammonium Tetrafluoroborates. A New Generation of Efficient Coupling Reagents Useful for Peptide Synthesis

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Chemoselective Activation of Nucleoside 3‘-O-Methylphosphonothioates with 1,3,5-Triazinyl Morpholinium Salts

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