Literature DB >> 19061365

Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.

William J Morris1, Matthew D Shair.   

Abstract

Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-beta-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-beta-glycosides in high yield and high selectivity. The high beta-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control.

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Year:  2009        PMID： 19061365      PMCID： PMC2699938          DOI： 10.1021/ol8022006

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


  10 in total

1.  One-pot synthesis of 2-deoxy-beta-oligosaccharides.

Authors:  R Pongdee; B Wu; G A Sulikowski
Journal:  Org Lett       Date:  2001-11-01       Impact factor: 6.005

2.  Stereospecific 1,2-migrations in carbohydrates. Stereocontrolled synthesis of .alpha.- and .beta.-2-deoxyglycosides.

Authors:  K C Nicolaou; T Ladduwahetty; J L Randall; A Chucholowski
Journal:  J Am Chem Soc       Date:  1986-04-01       Impact factor: 15.419

3.  Direct and stereoselective synthesis of beta-linked 2,6-deoxyoligosaccharides.

Authors:  Hiroshi Tanaka; Atsushi Yoshizawa; Takashi Takahashi
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Enantioselective synthesis of the central ring system of lomaiviticin A in the form of an unusually stable cyclic hydrate.

Authors:  Evan S Krygowski; Kerry Murphy-Benenato; Matthew D Shair
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Total synthesis of antigen bacillus anthracis tetrasaccharide--creation of an anthrax vaccine candidate.

Authors:  Daniel B Werz; Peter H Seeberger
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-07       Impact factor: 15.336

6.  De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

7.  Low-temperature X-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol: application of the variable oxygen probe to determine the relative sigma-donor ability of C-H and C-C bonds.

Authors:  Marisa Spiniello; Jonathan M White
Journal:  Org Biomol Chem       Date:  2003-09-07       Impact factor: 3.876

8.  Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides.

Authors:  Xin Xiong; Caroline Ovens; Adam W Pilling; John W Ward; Darren J Dixon
Journal:  Org Lett       Date:  2008-01-23       Impact factor: 6.005

9.  Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors.

Authors:  Timothy B Durham; William R Roush
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

10.  2-Deoxy-2-iodo-beta-glucopyranosyl fluorides: mild and highly stereoselective glycosyl donors for the synthesis of 2-deoxy-beta-glycosides from beta-hydroxy ketones.

Authors:  Nicolas Blanchard; William R Roush
Journal:  Org Lett       Date:  2003-01-09       Impact factor: 6.005
  10 in total
  14 in total

1.  Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation.

Authors:  Aleksandra Baranczak; Gary A Sulikowski
Journal:  Org Lett       Date:  2012-02-06       Impact factor: 6.005

Review 2.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

3.  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

4.  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

5.  Multigram Synthesis of 1-O-Acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-L-pyrrolosamine.

Authors:  Matthew Burk; Nolan Wilson; Seth B Herzon
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Stereocontrolled Synthesis of the Fully Glycosylated Monomeric Unit of Lomaiviticin A.

Authors:  Zhi Xu; Mikaela DiBello; Zechun Wang; John A Rose; Lei Chen; Xin Li; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2022-08-23       Impact factor: 16.383

7.  Development of enantioselective synthetic routes to (-)-kinamycin F and (-)-lomaiviticin aglycon.

Authors:  Christina M Woo; Shivajirao L Gholap; Liang Lu; Miho Kaneko; Zhenwu Li; P C Ravikumar; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2012-10-03       Impact factor: 15.419

8.  Steric control of alpha- and beta-alkylation of azulenone intermediates in a guanacastepene a synthesis.

Authors:  Hao Wang; Karol Michalak; Michał Michalak; Gonzalo Jiménez-Osés; J Wicha; K N Houk
Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354

9.  Structure Revision of the Lomaiviticins.

Authors:  Lee Joon Kim; Mengzhao Xue; Xin Li; Zhi Xu; Eric Paulson; Brandon Mercado; Hosea M Nelson; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2021-04-26       Impact factor: 15.419

10.  Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A.

Authors:  John A Rose; Subham Mahapatra; Xin Li; Chao Wang; Lei Chen; Steven M Swick; Seth B Herzon
Journal:  Chem Sci       Date:  2020-07-09       Impact factor: 9.825
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