Literature DB >> 35537215

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.

Shuai Meng1, Ishani Lakshika Hettiarachchi1, Bishwa Raj Bhetuwal1, Prakash Thapa1, Jianglong Zhu1.   

Abstract

Stereoselective synthesis of d-glycero- and l-glycero-β-d-mannoheptosides has been achieved by cesium carbonate-mediated β-selective anomeric O-alkylation of the corresponding d-mannoheptoses. In addition, this method has been utilized in the total synthesis of a tetrasaccharide repeat unit of Bacillus thermoaerophilus surface-layer glycoprotein.

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Year:  2022        PMID： 35537215      PMCID： PMC9166265          DOI： 10.1021/acs.joc.2c00168

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.198


  41 in total

1.  Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.

Authors:  David Crich; Abhisek Banerjee
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

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

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Padam P Acharya; Jianglong Zhu
Journal:  J Carbohydr Chem       Date:  2019-03-20       Impact factor: 1.667

3.  β-Mannosylation via O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Hai Nguyen; Xiaotian Qi; Cheng Fang; Kevin Saybolt; Xiaohua Li; Peng Liu; Jianglong Zhu
Journal:  European J Org Chem       Date:  2020-03-19

4.  Chemical Synthesis of d-glycero-d-manno-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation.

Authors:  Shinsuke Inuki; Toshihiko Aiba; Shota Kawakami; Taishin Akiyama; Jun-Ichiro Inoue; Yukari Fujimoto
Journal:  Org Lett       Date:  2017-05-25       Impact factor: 6.005

5.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354

6.  Stereoselective glycal fluorophosphorylation: synthesis of ADP-2-fluoroheptose, an inhibitor of the LPS biosynthesis.

Authors:  Hirofumi Dohi; Régis Périon; Maxime Durka; Michael Bosco; Yvain Roué; François Moreau; Sylvestre Grizot; Arnaud Ducruix; Sonia Escaich; Stéphane P Vincent
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

7.  Boronic-Acid-Catalyzed Regioselective and 1,2- cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism.

Authors:  Masamichi Tanaka; Akira Nakagawa; Nobuya Nishi; Kiyoko Iijima; Ryuichi Sawa; Daisuke Takahashi; Kazunobu Toshima
Journal:  J Am Chem Soc       Date:  2018-02-26       Impact factor: 15.419

8.  General Homologation Strategy for Synthesis of L-glycero- and D-glycero-Heptopyranoses.

Authors:  Shaheen K Mulani; Kuang-Chun Cheng; Kwok-Kong T Mong
Journal:  Org Lett       Date:  2015-11-11       Impact factor: 6.005

9.  Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-l-glycero-α-d-manno-heptopyranose.

Authors:  Christian Stanetty; Ian R Baxendale
Journal:  European J Org Chem       Date:  2015-03-10

10.  Synthesis of Rare 6-Deoxy-d-/l-Heptopyranosyl Fluorides: Assembly of a Hexasaccharide Corresponding to Campylobacter jejuni Strain CG8486 Capsular Polysaccharide.

Authors:  Tiantian Li; Jianjun Wang; Xinhao Zhu; Xin Zhou; Shaozi Sun; Peng Wang; Hongzhi Cao; Guangli Yu; Ming Li
Journal:  J Am Chem Soc       Date:  2021-07-14       Impact factor: 15.419
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