Literature DB >> 31396001

Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.

Shuai Meng1, Bishwa Raj Bhetuwal1, Padam P Acharya1, Jianglong Zhu1.   

Abstract

Synthesis of a variety of sugar lactols (hemiacetals) has been accomplished in moderate to excellent yields by using bromine-mediated oxidation of thioglycosides. It was found that acetonitrile is the optimal solvent for this oxidation reaction. This approach involving bromine as oxidant is superior to that using N-bromosuccimide (NBS) which produces byproduct succinimide often difficult to separate from the lactol products.

Entities:  

Keywords:  bromine; hemiacetals; oxidation; sugar lactols; thioglycosides

Year:  2019        PMID： 31396001      PMCID： PMC6686909          DOI： 10.1080/07328303.2019.1581889

Source DB:  PubMed          Journal:  J Carbohydr Chem        ISSN： 0732-8303            Impact factor:   1.667


  43 in total

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Authors:  Y J Kim; D Y Gin
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

3.  Synthesis of glycosyl-1-phosphates via dehydrative glycosylation.

Authors:  B A Garcia; D Y Gin
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

4.  Synthesis of 2,3:4,6-di-O-isopropylidene-D-allopyranose from D-glucose.

Authors:  Ana M Gómez; María D Company; Attila Agocs; Clara Uriel; Serafín Valverde; J Cristóbal López
Journal:  Carbohydr Res       Date:  2005-08-15       Impact factor: 2.104

5.  TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection.

Authors:  Minoru Izumi; Koichi Fukase; Shoichi Kusumoto
Journal:  Biosci Biotechnol Biochem       Date:  2002-01       Impact factor: 2.043

6.  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

7.  Ketone-imide versus ketone-oxime reductive cross-coupling promoted by samarium diiodide: new mechanistic insight gained from a failed aminocyclopentitol synthesis.

Authors:  Jose Luis Chiara; Angela García; Gabriella Cristóbal-Lumbroso
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

8.  Selective activation of glycosyl donors utilising electrochemical techniques: a study of the thermodynamic oxidation potentials of a range of chalcoglycosides.

Authors:  Robert R France; Neil V Rees; Jay D Wadhawan; Antony J Fairbanks; Richard G Compton
Journal:  Org Biomol Chem       Date:  2004-07-09       Impact factor: 3.876

9.  A palladium-catalyzed glycosylation reaction: the de novo synthesis of natural and unnatural glycosides.

Authors:  Ravula Satheesh Babu; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

10.  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
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  2 in total

1.  Stereoselective Synthesis of β-d-Manno-heptopyranoside via Cs2CO3-Mediated Anomeric O-Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Bacillus thermoaerophilus Surface-Layer Glycoprotein.

Authors:  Shuai Meng; Ishani Lakshika Hettiarachchi; Bishwa Raj Bhetuwal; Prakash Thapa; Jianglong Zhu
Journal:  J Org Chem       Date:  2022-05-10       Impact factor: 4.198

2.  Stereoselective Synthesis of 2-Azido-2-deoxy-β-d-mannosides via Cs2CO3-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Micrococcus luteus Teichuronic Acid.

Authors:  Bishwa Raj Bhetuwal; Fenglang Wu; Shuai Meng; Jianglong Zhu
Journal:  J Org Chem       Date:  2020-11-17       Impact factor: 4.354
  2 in total

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