Literature DB >> 10822541

3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.

H Li1, X Jiang, Y H Ye, C Fan, T Romoff, M Goodman.   

Abstract

[formula: see text] The new crystalline phosphate reagent 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) mediates amide bond formation with a remarkable resistance to racemization. Comparative racemization studies were carried out and DEPBT proved to be superior to typical phosphonium and uronium coupling reagents. DEPBT is easily prepared and is exceedingly stable with a shelf life of months at room temperature. The advantageous properties of DEPBT render it a useful and unique addition to the arsenal of coupling reagents.

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Year:  1999        PMID： 10822541     DOI： 10.1021/ol990573k

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


  33 in total

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4.  Next-Generation Total Synthesis of Vancomycin.

Authors:  Maxwell J Moore; Shiwei Qu; Ceheng Tan; Yu Cai; Yuzo Mogi; D Jamin Keith; Dale L Boger
Journal:  J Am Chem Soc       Date:  2020-09-04       Impact factor: 15.419

5.  Total synthesis of [Ψ[C(═S)NH]Tpg4]vancomycin aglycon, [Ψ[C(═NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

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Journal:  J Am Chem Soc       Date:  2012-01-06       Impact factor: 15.419

6.  Total synthesis and evaluation of [Psi[CH2NH]Tpg4]vancomycin aglycon: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

Authors:  Brendan M Crowley; Dale L Boger
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7.  Total synthesis and biological evaluation of transvalencin Z.

Authors:  Kathryn M Nelson; Christine E Salomon; Courtney C Aldrich
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Review 8.  Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues.

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9.  Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors:  John P Wolfe
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Authors:  Jorge E Zuniga; Jared T Hammill; Omri Drory; Jonathan E Nuss; James C Burnett; Rick Gussio; Peter Wipf; Sina Bavari; Axel T Brunger
Journal:  PLoS One       Date:  2010-06-30       Impact factor: 3.240
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