Literature DB >> 30019854

Direct Dehydrative Glycosylation of C1-Alcohols.

Sloane O'Neill1, Jacob Rodriguez1, Maciej A Walczak1.   

Abstract

Due to the central role played by carbohydrates in a multitude of biological processes, there has been a sustained interest in developing effective glycosylation methods to enable more thorough investigation of their essential functions. Among the myriad technologies available for stereoselective glycoside bond formation, dehydrative glycosylation possesses a distinct advantage given the unique properties of C1-alcohols such as straightforward preparation, stability, and a general reactivity compatible with a diverse set of reaction conditions. In this Focus Review, a survey of direct dehydrative glycosylations of C1-alcohols is provided with an emphasis on recent achievements, pervading limitations, mechanistic insights, and applications in total synthesis.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C1-alcohols; dehydrative; glycosides; glycosylation; synthetic methodology

Year:  2018        PMID: 30019854      PMCID: PMC7326538          DOI: 10.1002/asia.201800971

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  49 in total

1.  Straightforward glycosylation of alcohols and amino acids mediated by ionic liquid.

Authors:  Olivier Monasson; Gwenaëlle Sizun-Thomé; Nadège Lubin-Germain; Jacques Uziel; Jacques Augé
Journal:  Carbohydr Res       Date:  2012-03-10       Impact factor: 2.104

2.  Synthesis of (-)-hygromycin A: application of Mitsunobu glycosylation and tethered aminohydroxylation.

Authors:  Timothy J Donohoe; Aida Flores; Carole J R Bataille; Fátima Churruca
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 3.  Enzymatic glycosylation of small molecules: challenging substrates require tailored catalysts.

Authors:  Tom Desmet; Wim Soetaert; Pavla Bojarová; Vladimir Křen; Lubbert Dijkhuizen; Vanessa Eastwick-Field; Alexander Schiller
Journal:  Chemistry       Date:  2012-08-08       Impact factor: 5.236

Review 4.  Constrained saccharides: a review of structure, biology, and synthesis.

Authors:  Jacob Rodriguez; Sloane O'Neill; Maciej A Walczak
Journal:  Nat Prod Rep       Date:  2018-03-07       Impact factor: 13.423

5.  Direct dehydrative pyridylthio-glycosidation of unprotected sugars in aqueous media using 2-chloro-1,3-dimethylimidazolinium chloride as a condensing agent.

Authors:  Naoki Yoshida; Masato Noguchi; Tomonari Tanaka; Takeshi Matsumoto; Naoya Aida; Masaki Ishihara; Atsushi Kobayashi; Shin-ichiro Shoda
Journal:  Chem Asian J       Date:  2011-05-23

Review 6.  Design of α-Selective Glycopyranosyl Donors Relying on Remote Anchimeric Assistance.

Authors:  Bozhena S Komarova; Yury E Tsvetkov; Nikolay E Nifantiev
Journal:  Chem Rec       Date:  2016-01-20       Impact factor: 6.771

Review 7.  N-glycan and Alzheimer's disease.

Authors:  Yasuhiko Kizuka; Shinobu Kitazume; Naoyuki Taniguchi
Journal:  Biochim Biophys Acta Gen Subj       Date:  2017-04-29       Impact factor: 3.770

8.  Sulfide-mediated dehydrative glycosylation.

Authors:  H M Nguyen; Y Chen; S G Duron; D Y Gin
Journal:  J Am Chem Soc       Date:  2001-09-12       Impact factor: 15.419

Review 9.  Glycosylation in cancer: mechanisms and clinical implications.

Authors:  Salomé S Pinho; Celso A Reis
Journal:  Nat Rev Cancer       Date:  2015-08-20       Impact factor: 60.716

10.  An easy access to halide ion-catalytic alpha-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional reagents.

Authors:  Yuko Shingu; Yoshihiro Nishida; Hirofumi Dohi; Kazukiyo Kobayashi
Journal:  Org Biomol Chem       Date:  2003-07-21       Impact factor: 3.876

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  2 in total

1.  Organocatalytic enantioselective SN1-type dehydrative nucleophilic substitution: access to bis(indolyl)methanes bearing quaternary carbon stereocenters.

Authors:  Wen-Run Zhu; Qiong Su; Xiao-Yi Deng; Jia-Sheng Liu; Tao Zhong; Shan-Shui Meng; Ji-Tao Yi; Jiang Weng; Gui Lu
Journal:  Chem Sci       Date:  2021-11-23       Impact factor: 9.969

2.  Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate.

Authors:  Mei-Yuan Hsu; Sarah Lam; Chia-Hui Wu; Mei-Huei Lin; Su-Ching Lin; Cheng-Chung Wang
Journal:  Molecules       Date:  2020-03-02       Impact factor: 4.411

  2 in total

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