Literature DB >> 29572995

An Improved Approach to the Direct Construction of 2-Deoxy-β-Linked Sugars: Applications to Oligosaccharide Synthesis.

Dina Lloyd1, Clay S Bennett1.   

Abstract

A next-generation reagent-controlled approach for the synthesis of 2,6-dideoxy and 2,3,6-trideoxy sugar donors in good yield and high β-selectivity is reported. The use of p-toluenesulfonyl chloride and potassium hexamethyldisilazide (KHMDS) greatly simplifies deoxy-sugar glycoside construction, and can be used for gram-scale glycosylation reactions. The development of this approach and its application to the construction of β-linked deoxy-sugar oligosaccharides are described.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbohydrates; diastereoselectivity; glycosylation; oligosaccharides; synthetic methods

Mesh：

Substances：

Year:  2018        PMID： 29572995      PMCID： PMC6094935          DOI： 10.1002/chem.201800736

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  35 in total

1.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars.

Authors:  Jason M Nogueira; Marissa Bylsma; Danielle K Bright; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-19       Impact factor: 15.336

2.  Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.

Authors:  Yongho Park; Kaid C Harper; Nadine Kuhl; Eugene E Kwan; Richard Y Liu; Eric N Jacobsen
Journal:  Science       Date:  2017-01-13       Impact factor: 47.728

3.  Oxidative Activation of C-S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides.

Authors:  Annabel Kitowski; Ester Jiménez-Moreno; Míriam Salvadó; Jordi Mestre; Sergio Castillón; Gonzalo Jiménez-Osés; Omar Boutureira; Gonçalo J L Bernardes
Journal:  Org Lett       Date:  2017-09-28       Impact factor: 6.005

4.  Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance.

Authors:  Tobias Gylling Frihed; Mikael Bols; Christian Marcus Pedersen
Journal:  Chem Rev       Date:  2015-04-29       Impact factor: 60.622

5.  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

6.  A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides: Oligosaccharide Chain Length-Dependent Induction of Caspase-9-Mediated Apoptosis.

Authors:  Anand Krishnan V Iyer; Maoquan Zhou; Neelam Azad; Hosam Elbaz; Leo Wang; Derek K Rogalsky; Yon Rojanasakul; George A O'Doherty; Joseph M Langenhan
Journal:  ACS Med Chem Lett       Date:  2010-07-12       Impact factor: 4.345

Review 7.  Apoptolidin: induction of apoptosis by a natural product.

Authors:  Peter T Daniel; Ulrich Koert; Julia Schuppan
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-30       Impact factor: 15.336

8.  Cyclopropenium cation promoted dehydrative glycosylations using 2-deoxy- and 2,6-dideoxy-sugar donors.

Authors:  Jason M Nogueira; Son Hong Nguyen; Clay S Bennett
Journal:  Org Lett       Date:  2011-05-06       Impact factor: 6.005

9.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  De novo synthesis of the trisaccharide subunit of landomycins A and E.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  Org Lett       Date:  2008-05-08       Impact factor: 6.005
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  10 in total

1.  Recent Developments in Stereoselective Chemical Glycosylation.

Authors:  Jesse Ling; Clay S Bennett
Journal:  Asian J Org Chem       Date:  2019-05-02       Impact factor: 3.319

2.  Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors:  Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

3.  Synthesis of the Non-Reducing Hexasaccharide Fragment of Saccharomicin B.

Authors:  Manas Jana; Clay S Bennett
Journal:  Org Lett       Date:  2018-11-14       Impact factor: 6.005

4.  Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide.

Authors:  J Colin Mizia; Clay S Bennett
Journal:  Org Lett       Date:  2019-07-15       Impact factor: 6.005

5.  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

6.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.

Authors:  Joseph R Romeo; Luca McDermott; Clay S Bennett
Journal:  Org Lett       Date:  2020-04-13       Impact factor: 6.005

7.  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

8.  Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation.

Authors:  Jesse Ling; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336

9.  Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations.

Authors:  Ming-Hua Zhuo; David J Wilbur; Eugene E Kwan; Clay S Bennett
Journal:  J Am Chem Soc       Date:  2019-10-09       Impact factor: 15.419

10.  Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst.

Authors:  Abhijit Sau; Carlos Palo-Nieto; M Carmen Galan
Journal:  J Org Chem       Date:  2019-02-15       Impact factor: 4.354
  10 in total

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