Literature DB >> 31755271

Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Subbarao Yalamanchili1, William Miller1, Xizhao Chen1, Clay S Bennett1.   

Abstract

A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-pyran-4-ones in good to excellent yields (71-90%). These latter compounds can be easily converted into a number of otherwise difficult to access 2,6-dideoxy sugars.

Entities:  

Year:  2019        PMID： 31755271      PMCID： PMC6956608          DOI： 10.1021/acs.orglett.9b03812

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


  42 in total

Review 1.  The role of carbohydrates in biologically active natural products.

Authors:  A C Weymouth-Wilson
Journal:  Nat Prod Rep       Date:  1997-04       Impact factor: 13.423

2.  Flexible Tetrahydropyran Synthesis from Homopropargylic Alcohols Using Sequential Pd-Au Catalysis.

Authors:  Jungjoon Kim; Wook Jeong; Young Ho Rhee
Journal:  Org Lett       Date:  2016-12-22       Impact factor: 6.005

3.  Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine.

Authors:  Kathlyn A Parker; Wonsuk Chang
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

4.  Saccharomicins, novel heptadecaglycoside antibiotics produced by Saccharothrix espanaensis: antibacterial and mechanistic activities.

Authors:  M P Singh; P J Petersen; W J Weiss; F Kong; M Greenstein
Journal:  Antimicrob Agents Chemother       Date:  2000-08       Impact factor: 5.191

5.  De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups.

Authors:  Ravula Satheesh Babu; Qian Chen; Sang-Woo Kang; Maoquan Zhou; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419

6.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

7.  Synthesis of enantioenriched propargylic alcohols related to polyketide natural products. A comparison of methodologies.

Authors:  James A Marshall; Matthew P Bourbeau
Journal:  Org Lett       Date:  2003-09-04       Impact factor: 6.005

8.  Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B.

Authors:  Marissa Bylsma; Clay S Bennett
Journal:  Org Lett       Date:  2018-07-17       Impact factor: 6.005

9.  De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction.

Authors:  Ravula Satheesh Babu; Maoquan Zhou; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

10.  Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives.

Authors:  Chandraiah Lagisetti; Maria V Yermolina; Lalit Kumar Sharma; Gustavo Palacios; Brett J Prigaro; Thomas R Webb
Journal:  ACS Chem Biol       Date:  2013-12-30       Impact factor: 5.100
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  3 in total

1.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

2.  Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

Authors:  Subbarao Yalamanchili; Tu-Anh V Nguyen; Nicola L B Pohl; Clay S Bennett
Journal:  Org Biomol Chem       Date:  2020-05-06       Impact factor: 3.876

3.  De Novo Synthesis of an l-Lemonose Thioglycoside Donor from d-Threonine.

Authors:  Eric D Huseman; Steven D Townsend
Journal:  Tetrahedron Lett       Date:  2021-04-22       Impact factor: 2.032
  3 in total

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