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Literature DB >> 12762674

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

Abstract

[reaction: see text] A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

Entities: Chemical

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Year: 2003 PMID： 12762674 DOI： 10.1021/ol034393t

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

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Cited

11 in total

1. Total synthesis of (-)-spinosyn A.

Authors: Dustin J Mergott; Scott A Frank; William R Roush
Journal: Proc Natl Acad Sci U S A Date: 2004-06-01 Impact factor: 11.205

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. Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.

Authors: Krystyna M Demkiw; Wouter A Remmerswaal; Thomas Hansen; Gijsbert A van der Marel; Jeroen D C Codée; K A Woerpel
Journal: Angew Chem Int Ed Engl Date: 2022-09-16 Impact factor: 16.823

4. Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals.

Authors: Krystyna M Demkiw; Chunhua T Hu; K A Woerpel
Journal: J Org Chem Date: 2022-04-01 Impact factor: 4.198

5. The effect of electrostatic interactions on conformational equilibria of multiply substituted tetrahydropyran oxocarbenium ions.

Authors: Michael T Yang; K A Woerpel
Journal: J Org Chem Date: 2009-01-16 Impact factor: 4.354

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

1. Total synthesis of (-)-spinosyn A.

Review 2. Methods for 2-Deoxyglycoside Synthesis.

3. Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.

4. Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals.

5. The effect of electrostatic interactions on conformational equilibria of multiply substituted tetrahydropyran oxocarbenium ions.

6. Direct and stereoselective synthesis of alpha-linked 2-deoxyglycosides.

7. Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates.

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

9. Synthesis of a 2"-deoxy-β-GalCer.

10. A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides.