Literature DB >> 28672165

Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides.

Philip O Adero1, Dean R Jarois1, David Crich2.   

Abstract

With the aid of a series of model thioether or thioglycoside containing polyols protected with combinations of benzyl ethers and 2-naphthylmethyl ethers it is demonstrated that the latter are readily cleaved selectively under hydrogenolytic conditions in the presence of the frequently catalyst-poisoning sulfides. These results suggest the possibility of employing 2-naphthylmethyl ethers in place of benzyl ethers in synthetic schemes when hydrogenolytic deprotection is anticipated in the presence of thioether type functionality.
Copyright © 2017 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Benzyl ethers; Hydrogenolysis; Naphthylmethyl ethers; Thioethers; Thioglycosides

Mesh：

Substances：

Year:  2017        PMID： 28672165      PMCID： PMC5572532          DOI： 10.1016/j.carres.2017.06.011

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  9 in total

1.  New insight on 2-naphthylmethyl (NAP) ether as a protecting group in carbohydrate synthesis: a divergent approach towards a high-mannose type oligosaccharide library.

Authors:  Yao Li; Bimalendu Roy; Xinyu Liu
Journal:  Chem Commun (Camb)       Date:  2011-07-07       Impact factor: 6.222

2.  Synthesis of di- to hexasaccharide 1,2-linked beta-mannopyranan oligomers, a terminal S-linked tetrasaccharide congener and the corresponding BSA glycoconjugates.

Authors:  M Nitz; D R Bundle
Journal:  J Org Chem       Date:  2001-12-14       Impact factor: 4.354

3.  Direct stereoselective synthesis of beta-thiomannosides.

Authors:  D Crich; H Li
Journal:  J Org Chem       Date:  2000-02-11       Impact factor: 4.354

4.  The 5-deoxy-5-methylthio-xylofuranose residue in mycobacterial lipoarabinomannan. absolute stereochemistry, linkage position, conformation, and immunomodulatory activity.

Authors:  Maju Joe; Daniel Sun; Hashem Taha; Gladys C Completo; Joanne E Croudace; David A Lammas; Gurdyal S Besra; Todd L Lowary
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

5.  Interfacial cavity filling to optimize CD4-mimetic miniprotein interactions with HIV-1 surface glycoprotein.

Authors:  Laurence Morellato-Castillo; Priyamvada Acharya; Olivier Combes; Johan Michiels; Anne Descours; Oscar H P Ramos; Yongping Yang; Guido Vanham; Kevin K Ariën; Peter D Kwong; Loïc Martin; Pascal Kessler
Journal:  J Med Chem       Date:  2013-06-11       Impact factor: 7.446

6.  A highly efficient azide-based protecting group for amines and alcohols.

Authors:  Srinivasu Pothukanuri; Nicolas Winssinger
Journal:  Org Lett       Date:  2007-05-05       Impact factor: 6.005

7.  Chemical synthesis of 6'-alpha-maltosyl-maltotriose, a branched oligosaccharide representing the branch point of starch.

Authors:  M S Motawia; C E Olsen; K Enevoldsen; J Marcussen; B L Møller
Journal:  Carbohydr Res       Date:  1995-11-07       Impact factor: 2.104

8.  Chemoselective Cleavage of p-Methoxybenzyl and 2-Naphthylmethyl Ethers Using a Catalytic Amount of HCl in Hexafluoro-2-propanol.

Authors:  Anne Geert Volbeda; Hans A V Kistemaker; Herman S Overkleeft; Gijsbert A van der Marel; Dmitri V Filippov; Jeroen D C Codée
Journal:  J Org Chem       Date:  2015-08-14       Impact factor: 4.354

9.  Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene.

Authors:  Dina Lloyd; Marissa Bylsma; Danielle K Bright; Xizhao Chen; Clay S Bennett
Journal:  J Org Chem       Date:  2017-03-27       Impact factor: 4.354
  9 in total

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