Literature DB >> 11531118

Highly efficient deacetylation by use of the neutral organotin catalyst [tBu2SnOH(Cl)]2.

A Orita1, Y Hamada, T Nakano, S Toyoshima, J Otera.   

Abstract

Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu2SnOH(Cl)]2. The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.

Entities:  

Year:  2001        PMID: 11531118     DOI: 10.1002/1521-3765(20010803)7:15<3321::aid-chem3321>3.0.co;2-h

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  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

2.  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

3.  Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B.

Authors:  Guojun Pan; Robert M Williams
Journal:  J Org Chem       Date:  2012-05-07       Impact factor: 4.354

4.  A unified strategy for enantioselective total synthesis of cladiellin and briarellin diterpenes: total synthesis of briarellins E and F and the putative structure of alcyonin and revision of its structure assignment.

Authors:  Olivier Corminboeuf; Larry E Overman; Lewis D Pennington
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

5.  Concise synthesis of capuramycin.

Authors:  Michio Kurosu; Kai Li; Dean C Crick
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

6.  Stereocontrolled Total Synthesis of Muraymycin D1 Having a Dual Mode of Action against Mycobacterium tuberculosis.

Authors:  Katsuhiko Mitachi; Bilal A Aleiwi; Christopher M Schneider; Shajila Siricilla; Michio Kurosu
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

7.  Investigation of acetyl migrations in furanosides.

Authors:  O P Chevallier; M E Migaud
Journal:  Beilstein J Org Chem       Date:  2006-07-21       Impact factor: 2.883

  7 in total

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