Literature DB >> 18529028

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

David Crich1, Maheswaran S Karatholuvhu.   

Abstract

4-Trifluoromethylbenzenepropargyl ethers are stable and sterically minimal alcohol protecting groups that are readily cleaved in a single step by exposure to lithium naphthalenide. In conjunction with the 4,6-O-benzylidene protecting group, glycosylation reactions of 2-O-(4-trifluoromethylbenzenepropargyl)-protected mannosyl donors are extremely beta-selective.

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Year:  2008        PMID： 18529028      PMCID： PMC2742709          DOI： 10.1021/jo7023398

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


  7 in total

1.  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

2.  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

3.  2-O-propargyl ethers: readily cleavable, minimally intrusive protecting groups for beta-mannosyl donors.

Authors:  David Crich; Prasanna Jayalath
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

4.  Novel 5-(3-aryl-2-propynyl)-5-(arylsulfonyl)thiazolidine-2,4-diones as antihyperglycemic agents.

Authors:  J Wrobel; Z Li; A Dietrich; M McCaleb; B Mihan; J Sredy; D Sullivan
Journal:  J Med Chem       Date:  1998-03-26       Impact factor: 7.446

5.  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

6.  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

7.  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
  7 in total
  7 in total

1.  Application of a new phosphorus-free palladium heterogeneous nanocatalyst supported on modified MWCNT the highly selective and efficient cleavage of propargyl, allyl, and benzyl phenol ethers under mild conditions.

Authors:  Hashem Sharghi; Abbas Khoshnood; Reza Khalifeh; Mohammad Mehdi Doroodmand
Journal:  Mol Divers       Date:  2015-04-17       Impact factor: 2.943

2.  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

3.  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

4.  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

Review 5.  Protecting groups in carbohydrate chemistry: influence on stereoselectivity of glycosylations.

Authors:  Jian Guo; Xin-Shan Ye
Journal:  Molecules       Date:  2010-10-20       Impact factor: 4.411

6.  Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations.

Authors:  Ming-Hua Zhuo; David J Wilbur; Eugene E Kwan; Clay S Bennett
Journal:  J Am Chem Soc       Date:  2019-10-09       Impact factor: 15.419

Review 7.  Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis.

Authors:  Martin A Fascione; Robin Brabham; W Bruce Turnbull
Journal:  Chemistry       Date:  2016-01-07       Impact factor: 5.236
  7 in total

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