Literature DB >> 17020326

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

David Crich1, Baolin Wu.   

Abstract

[reaction: see text] The (1-naphthyl)propargyl group is introduced as a sterically unobtrusive alcohol protecting group that is cleaved in a single step by exposure to dichlorodicyanoquinone in wet dichloromethane. In conjunction with the 4,6-O-benzylidene protecting group, and the use of the sulfoxide glycosylation method, 3-O-naphthylpropargyl-protected mannosyl donors are extremely beta-selective.

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Year:  2006        PMID： 17020326      PMCID： PMC2615467          DOI： 10.1021/ol061938l

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


  22 in total

1.  Synthesis of a model compound related to an anti-ulcer pectic polysaccharide.

Authors:  M Maruyama; T Takeda; N Shimizu; N Hada; H Yamada
Journal:  Carbohydr Res       Date:  2000-04-07       Impact factor: 2.104

2.  1,2-diacetals: a new opportunity for organic synthesis.

Authors:  S V Ley; D K Baeschlin; D J Dixon; A C Foster; S J Ince; H W Priepke; D J Reynolds
Journal:  Chem Rev       Date:  2001-01       Impact factor: 60.622

3.  Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation. 2-Picolinyl ethers as reactivity-enhancing replacements for benzyl ethers.

Authors:  D Crich; V Dudkin
Journal:  J Am Chem Soc       Date:  2001-07-18       Impact factor: 15.419

4.  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

5.  Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: ring inversion of an alpha-xylopyranosyl sulfoxide dependent on the configuration at sulfur.

Authors:  David Crich; Jan Mataka; Lev N Zakharov; Arnold L Rheingold; Donald J Wink
Journal:  J Am Chem Soc       Date:  2002-05-29       Impact factor: 15.419

6.  Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Authors:  Jeroen D C Codée; Remy E J N Litjens; René den Heeten; Herman S Overkleeft; Jacques H van Boom; Gijs A van der Marel
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

7.  Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II): application to Sonogashira cross-coupling reactions.

Authors:  Robert A Batey; Ming Shen; Alan J Lough
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

8.  The 3,4-O-carbonate protecting group as a beta-directing group in rhamnopyranosylation in both homogeneous and heterogeneous glycosylations as compared to the chameleon-like 2,3-O-carbonates.

Authors:  David Crich; A U Vinod; John Picione
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

9.  Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide.

Authors:  Moloy Banerjee; Sujit Roy
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

10.  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
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  14 in total

1.  Synthesis and structural verification of the xylomannan antifreeze substance from the freeze-tolerant Alaskan beetle Upis ceramboides.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  J Org Chem       Date:  2011-10-07       Impact factor: 4.354

2.  Convergent synthesis of a beta-(1-->3)-mannohexaose.

Authors:  David Crich; Baolin Wu; Prasanna Jayalath
Journal:  J Org Chem       Date:  2007-08-01       Impact factor: 4.354

3.  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

4.  Further studies on cation clock reactions in glycosylation: observation of a configuration specific intramolecular sulfenyl transfer and isolation and characterization of a tricyclic acetal.

Authors:  Min Huang; Takayuki Furukawa; Pascal Retailleau; David Crich; Luis Bohé
Journal:  Carbohydr Res       Date:  2016-04-06       Impact factor: 2.104

5.  Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.

Authors:  Philip O Adero; Takayuki Furukawa; Min Huang; Debaraj Mukherjee; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2015-08-07       Impact factor: 15.419

6.  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

7.  Cation clock permits distinction between the mechanisms of α- and β-O- and β-C-glycosylation in the mannopyranose series: evidence for the existence of a mannopyranosyl oxocarbenium ion.

Authors:  Min Huang; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2012-08-31       Impact factor: 15.419

8.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354

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

Authors:  David Crich; Linfeng Li; Michio Shirai
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

10.  Synthetic Carbohydrate Chemistry and Translational Medicine.

Authors:  Sachin S Shivatare; Chi-Huey Wong
Journal:  J Org Chem       Date:  2020-10-30       Impact factor: 4.354
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