Literature DB >> 19243158

The 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group: a new alcohol protecting group, fully orthogonal with the p-methoxybenzyl group and removable under desilylation conditions.

David Crich1, Linfeng Li, Michio Shirai.   

Abstract

A new benzyl ether-type protecting group for alcohols, the 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group, is introduced. The protecting group is introduced by means of the readily prepared benzyl bromide and is cleaved with tetrabutylammonium fluoride in dimethylformamide under microwave irradiation. The fluoride substituent provides stability to oxidizing conditions, such that the new protecting group is fully compatible with the removal of p-methoxybenzyl ethers with DDQ. Applications of the new protecting group in the direct stereocontrolled synthesis of beta-mannopyranosides are presented.

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Year:  2009        PMID： 19243158      PMCID： PMC3102264          DOI： 10.1021/jo900026e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  17 in total

1.  1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors:  D Crich; M Smith
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

2.  Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

Authors:  David Crich; Prasanna Jayalath; Thomas K Hutton
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

3.  1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylation.

Authors:  David Crich; Baolin Wu
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

4.  p-Siletanylbenzylidene acetal: oxidizable protecting group for diols.

Authors:  Sarah E House; Kevin W C Poon; Hubert Lam; Gregory B Dudley
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

5.  IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE.

Authors:  David Crich; Abhisek Banerjee; Wenju Li; Qingjia Yao
Journal:  J Carbohydr Chem       Date:  2005       Impact factor: 1.667

6.  Chemical synthesis of normal and transformed PSA glycopeptides.

Authors:  Vadim Y Dudkin; Justin S Miller; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2004-01-28       Impact factor: 15.419

7.  Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylation.

Authors:  David Crich; Maheswaran S Karatholuvhu
Journal:  J Org Chem       Date:  2008-06-05       Impact factor: 4.354

8.  Mechanism of 4,6-O-benzylidene-directed beta-mannosylation as determined by alpha-deuterium kinetic isotope effects.

Authors:  David Crich; N Susantha Chandrasekera
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-11       Impact factor: 15.336

9.  Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652.

Authors:  David Crich; Qingjia Yao
Journal:  J Am Chem Soc       Date:  2004-07-07       Impact factor: 15.419

10.  Direct chemical synthesis of the beta-mannans: linear and block syntheses of the alternating beta-(1-->3)-beta-(1-->4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa.

Authors:  David Crich; Wenju Li; Hongmei Li
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419
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  1 in total

1.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354
  1 in total

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