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Literature DB >> 10990433

Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.

Abstract

[reaction: see text]This letter describes a single flask strategy to the synthesis of alpha-C-glycosides from glycals. This protocol couples a glycal epoxidation reaction with a C-2 alkoxy-directed carbon-carbon bond-forming reaction.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2000 PMID： 10990433 DOI： 10.1021/ol006286u

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

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Cited

9 in total

1. Total synthesis of theopederin D.

Authors: Michael E Green; Jason C Rech; Paul E Floreancig
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

Authors: Laura Alberch; Gang Cheng; Seung-Kee Seo; Xuehua Li; Fabien P Boulineau; Alexander Wei
Journal: J Org Chem Date: 2011-03-18 Impact factor: 4.354

3. Total synthesis of brevenal.

Authors: Yuan Zhang; John Rohanna; Jie Zhou; Karthik Iyer; Jon D Rainier
Journal: J Am Chem Soc Date: 2011-02-15 Impact factor: 15.419

4. Exploring a sulfone linker utilizing trimethyl aluminum as a cleavage reagent: solid-phase synthesis of sulfonamides and ureas.

Authors: Tsai-Wen Chung; Chih-Hau Chen; Chu-Chung Lin; Hsien-Jen Wu; Chung-Ming Sun; Wen-Sheng Chung
Journal: Mol Divers Date: 2012-06-30 Impact factor: 2.943

9. 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities.

Authors: Mohamed Mohamed El-Sadek; Seham Yassen Hassan; Nagwa Said Abd El-Dayem; Galila Ahmed Yacout
Journal: Molecules Date: 2012-06-07 Impact factor: 4.411

9 in total

Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.

1. Total synthesis of theopederin D.

2. Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

3. Total synthesis of brevenal.

4. Exploring a sulfone linker utilizing trimethyl aluminum as a cleavage reagent: solid-phase synthesis of sulfonamides and ureas.

5. Mirror-image carbohydrates: synthesis of the unnatural enantiomer of a blood group trisaccharide.

6. syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.

7. A method for the preparation of differentiated trans-1,2-diol derivatives with enantio- and diastereocontrol.

8. Synthesis and reactivity of 4'-deoxypentenosyl disaccharides.

9. 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities.