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Literature DB >> 16149811

Glycosylation with trichloroacetimidates in ionic liquids: influence of the reaction medium on the stereochemical outcome.

Anna Rencurosi¹, Luigi Lay, Giovanni Russo, Enrico Caneva, Laura Poletti.

Abstract

[reactions: see text] The glycosylation with trichloroacetimidates derived from different glycopyranoses bearing a nonparticipating group at C-2 was explored in different ionic liquids as solvents. The stereoselectivity of the reaction was significantly affected by the reaction media and by the anomeric configuration of the donor.

Entities: Chemical Gene Species

Year: 2005 PMID： 16149811 DOI： 10.1021/jo050704x

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

7 in total

1. Glycosylation in room temperature ionic liquid using unprotected and unactivated donors.

Authors: Tae-Joon Park; Michel Weïwer; Xuejun Yuan; Sultan N Baytas; Eva M Munoz; Saravanababu Murugesan; Robert J Linhardt
Journal: Carbohydr Res Date: 2006-11-29 Impact factor: 2.104

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

Authors: Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal: Chem Rev Date: 2018-05-30 Impact factor: 60.622

3. Rapid assembly of oligosaccharides: a highly convergent strategy for the assembly of a glycosylated amino acid derived from PSGL-1.

Authors: Yusuf Vohra; Therese Buskas; Geert-Jan Boons
Journal: J Org Chem Date: 2009-08-21 Impact factor: 4.354

Glycosylation with trichloroacetimidates in ionic liquids: influence of the reaction medium on the stereochemical outcome.

1. Glycosylation in room temperature ionic liquid using unprotected and unactivated donors.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

3. Rapid assembly of oligosaccharides: a highly convergent strategy for the assembly of a glycosylated amino acid derived from PSGL-1.

4. One-pot synthesis of oligosaccharides by combining reductive openings of benzylidene acetals and glycosylations.

5. Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

6. Self-promoted and stereospecific formation of N-glycosides.

7. Click reactions as a key step for an efficient and selective synthesis of D-xylose-based ILs.

Glycosylation with trichloroacetimidates in ionic liquids: influence of the reaction medium on the stereochemical outcome.

1. Glycosylation in room temperature ionic liquid using unprotected and unactivated donors.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

3. Rapid assembly of oligosaccharides: a highly convergent strategy for the assembly of a glycosylated amino acid derived from PSGL-1.

4. One-pot synthesis of oligosaccharides by combining reductive openings of benzylidene acetals and glycosylations.

5. Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

6. Self-promoted and stereospecific formation of N-glycosides.

7. Click reactions as a key step for an efficient and selective synthesis of D-xylose-based ILs.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.