Literature DB >> 28437118

Blue Light Photocatalytic Glycosylation without Electrophilic Additives.

Peng Wen1, David Crich1.   

Abstract

Photocatalytic formation of glycosidic bonds employing stable and readily accessible O-glycosyl derivatives of 2,2,6,6-tetramethylpiperidin-1-ol is presented that employs an iridium-based photocatalyst and blue LEDs. The reaction proceeds at room temperature and in the absence of additives other than 4 Å molecular sieves. Stereoselectivities are modest but nevertheless dependent on the anomeric configuration of the donor, suggesting a substantial degree of concerted character.

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Year:  2017        PMID: 28437118      PMCID: PMC5538785          DOI: 10.1021/acs.orglett.7b00932

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


  32 in total

1.  Visible light mediated activation and O-glycosylation of thioglycosides.

Authors:  Walter J Wever; Maris A Cinelli; Albert A Bowers
Journal:  Org Lett       Date:  2012-12-20       Impact factor: 6.005

2.  Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates.

Authors:  Kyan A D'Angelo; Mark S Taylor
Journal:  J Am Chem Soc       Date:  2016-08-17       Impact factor: 15.419

3.  Mapping the Reactivity and Selectivity of 2-Azidofucosyl Donors for the Assembly of N-Acetylfucosamine-Containing Bacterial Oligosaccharides.

Authors:  Bas Hagen; Sara Ali; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  J Org Chem       Date:  2017-01-10       Impact factor: 4.354

4.  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

Review 5.  A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Authors:  Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2014-07-01       Impact factor: 2.104

6.  Visible Light Photoredox-Catalyzed O-Sialylation Using Thiosialoside Donors.

Authors:  Yang Yu; De-Cai Xiong; Run-Ze Mao; Xin-Shan Ye
Journal:  J Org Chem       Date:  2016-06-15       Impact factor: 4.354

7.  Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid.

Authors:  Tomoya Kimura; Takahiro Eto; Daisuke Takahashi; Kazunobu Toshima
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

8.  Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization Reactions.

Authors:  Yaroslav Ya Khomutnyk; Alonso J Argüelles; Grace A Winschel; Zhankui Sun; Paul M Zimmerman; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2015-12-23       Impact factor: 15.419

9.  IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: a new pair of semiorthogonal glycosyl donors.

Authors:  J Cristóbal López; Clara Uriel; Alejandra Guillamón-Martín; Serafín Valverde; Ana M Gómez
Journal:  Org Lett       Date:  2007-06-20       Impact factor: 6.005

10.  Probing the influence of protecting groups on the anomeric equilibrium in sialic acid glycosides with the persistent radical effect.

Authors:  Pavan K Kancharla; Takayuki Kato; David Crich
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419

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  2 in total

1.  A sustainable innovation for the tandem synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL IM from Thermomyces lanuginosus in continuous-flow microreactors.

Authors:  Li-Hua Du; Ping-Feng Chen; Rui-Jie Long; Miao Xue; Xi-Ping Luo
Journal:  RSC Adv       Date:  2020-04-02       Impact factor: 4.036

2.  Site-selective redox isomerizations of furanosides using a combined arylboronic acid/photoredox catalyst system.

Authors:  Victoria Dimakos; Daniel Gorelik; Hsin Y Su; Graham E Garrett; Gregory Hughes; Hiromitsu Shibayama; Mark S Taylor
Journal:  Chem Sci       Date:  2020-01-03       Impact factor: 9.825

  2 in total

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