Literature DB >> 22937741

Selective esterifications of primary alcohols in a water-containing solvent.

Yong Wang1, Bilal A Aleiwi, Qinghui Wang, Michio Kurosu.   

Abstract

Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO(3), and Oxyma or Oxyma derivative 5b in 5% H(2)O-CH(3)CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.

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Year:  2012        PMID： 22937741      PMCID： PMC3563398          DOI： 10.1021/ol3022337

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


  8 in total

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Authors:  Alan C Spivey; Stellios Arseniyadis
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-18       Impact factor: 15.336

2.  Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.

Authors:  Ramon Subirós-Funosas; Rafel Prohens; Rafael Barbas; Ayman El-Faham; Fernando Albericio
Journal:  Chemistry       Date:  2009-09-21       Impact factor: 5.236

3.  Synthesis of ureidomuraymycidine derivatives for structure-activity relationship studies of muraymycins.

Authors:  Bilal A Aleiwi; Christopher M Schneider; Michio Kurosu
Journal:  J Org Chem       Date:  2012-04-06       Impact factor: 4.354

4.  A reliable Pd-mediated hydrogenolytic deprotection of BOM group of uridine ureido nitrogen.

Authors:  Bilal A Aleiwi; Michio Kurosu
Journal:  Tetrahedron Lett       Date:  2012-05-12       Impact factor: 2.415

5.  Facile synthesis of a library of Lyme disease glycolipid antigens.

Authors:  Jean-d'Amour K Twibanire; Raha Parvizi Omran; T Bruce Grindley
Journal:  Org Lett       Date:  2012-07-11       Impact factor: 6.005

6.  Efficient and controllably selective preparation of esters using uronium-based coupling agents.

Authors:  Jean-d'Amour K Twibanire; T Bruce Grindley
Journal:  Org Lett       Date:  2011-05-19       Impact factor: 6.005

7.  A new Oxyma derivative for nonracemizable amide-forming reactions in water.

Authors:  Qinghui Wang; Yong Wang; Michio Kurosu
Journal:  Org Lett       Date:  2012-06-14       Impact factor: 6.005

8.  Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf.

Authors:  Michio Kurosu; Kai Li
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354
  8 in total
  10 in total

1.  Substrate Tolerance of Bacterial Glycosyltransferase MurG: Novel Fluorescence-Based Assays.

Authors:  Katsuhiko Mitachi; Hyun Gi Yun; Cody D Gillman; Karolina Skorupinska-Tudek; Ewa Swiezewska; William M Clemons; Michio Kurosu
Journal:  ACS Infect Dis       Date:  2019-12-11       Impact factor: 5.084

2.  Improved synthesis of capuramycin and its analogues.

Authors:  Yong Wang; Shajila Siricilla; Bilal A Aleiwi; Michio Kurosu
Journal:  Chemistry       Date:  2013-09-06       Impact factor: 5.236

3.  Mild and convenient N-formylation protocol in water-containing solvents.

Authors:  Bilal A Aleiwi; Katsuhiko Mitachi; Michio Kurosu
Journal:  Tetrahedron Lett       Date:  2013-04-17       Impact factor: 2.415

4.  A New Combination of a Pleuromutilin Derivative and Doxycycline for Treatment of Multidrug-Resistant Acinetobacter baumannii.

Authors:  Shajila Siricilla; Katsuhiko Mitachi; Junshu Yang; Shakiba Eslamimehr; Maddie R Lemieux; Bernd Meibohm; Yinduo Ji; Michio Kurosu
Journal:  J Med Chem       Date:  2017-03-22       Impact factor: 7.446

5.  Oxyma-based phosphates for racemization-free peptide segment couplings.

Authors:  Katsuhiko Mitachi; Yuki E Kurosu; Brandon T Hazlett; Michio Kurosu
Journal:  J Pept Sci       Date:  2016-03       Impact factor: 1.905

6.  Structure determination of lipopeptides from Mycobacterium avium subspecies paratuberculosis and identification of antigenic lipopeptide probes.

Authors:  Katsuhiko Mitachi; Lekh Nath Sharma Gautam; Jeffrey H Rice; Keiko Eda; Ashutosh Wadhwa; Eiichi Momotani; Joseph P Hlopak; Shigetoshi Eda; Michio Kurosu
Journal:  Anal Biochem       Date:  2016-04-22       Impact factor: 3.365

7.  Semisynthesis of an Anticancer DPAGT1 Inhibitor from a Muraymycin Biosynthetic Intermediate.

Authors:  Katsuhiko Mitachi; Shou M Kurosu; Shakiba Eslamimehr; Maddie R Lemieux; Yoshimasa Ishizaki; William M Clemons; Michio Kurosu
Journal:  Org Lett       Date:  2019-01-30       Impact factor: 6.005

8.  Synthesis, Crystal Structure, and Biological Activity of Ethyl 4-Methyl-2,2-dioxo-1H-2λ⁶,1-benzothiazine-3-carboxylate Polymorphic Forms.

Authors:  Igor V Ukrainets; Anna A Burian; Vyacheslav N Baumer; Svitlana V Shishkina; Lyudmila V Sidorenko; Igor A Tugaibei; Natali I Voloshchuk; Pavlo S Bondarenko
Journal:  Sci Pharm       Date:  2018-05-30

9.  An antimycobacterial pleuromutilin analogue effective against dormant bacilli.

Authors:  Maddie R Lemieux; Shajila Siricilla; Katsuhiko Mitachi; Shakiba Eslamimehr; Yuehong Wang; Dong Yang; Jeffrey D Pressly; Ying Kong; Frank Park; Scott G Franzblau; Michio Kurosu
Journal:  Bioorg Med Chem       Date:  2018-08-18       Impact factor: 3.641

10.  A practical synthesis of a novel DPAGT1 inhibitor, aminouridyl phenoxypiperidinbenzyl butanamide (APPB) for in vivo studies.

Authors:  Katsuhiko Mitachi; Shou M Kurosu; Cody D Gillman; Hyun Gi Yun; William M Clemons; Michio Kurosu
Journal:  MethodsX       Date:  2019-09-27
  10 in total

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