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Literature DB >> 17375956

Facile oxidative cleavage of 4-O-benzyl ethers with dichlorodicyanoquinone in rhamno- and mannopyranosides.

Abstract

On exposure to dichlorodicyanoquinone in wet dichloromethane at room temperature, equatorial 4-O-benzyl ethers are removed with moderate selectivity in the presence of other benzyl ethers in glycopyranosides and glycothiopyranosides.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17375956 PMCID： PMC2615469 DOI： 10.1021/jo062411p

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

17 in total

1. Total synthesis of epothilone A.

Authors: B Zhu; J S Panek
Journal: Org Lett Date: 2000-08-24 Impact factor: 6.005

2. Synthesis of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene: a caveat.

Authors: Christian Girard; Marie-Laure Miramon; Tanguy de Solminihac; Jean Herscovici
Journal: Carbohydr Res Date: 2002-10-11 Impact factor: 2.104

3. The disarming effect of the 4,6-acetal group on glycoside reactivity: torsional or electronic?

Authors: Henrik Helligsø Jensen; Lars Ulrik Nordstrøm; Mikael Bols
Journal: J Am Chem Soc Date: 2004-08-04 Impact factor: 15.419

4. 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

5. Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

Authors: David Crich; Prasanna Jayalath; Thomas K Hutton
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

6. Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1.

Authors: Vince Pozsgay
Journal: J Org Chem Date: 1998-08-21 Impact factor: 4.354

7. A simple method for avoiding alkylthio group migration during the synthesis of thioglycoside 2,3-orthoesters. An improved synthesis of partially acylated 1-thio-alpha-L-rhamnopyranosides.

Authors: V Pozsgay
Journal: Carbohydr Res Date: 1992-11-04 Impact factor: 2.104

8. Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652.

Authors: David Crich; Qingjia Yao
Journal: J Am Chem Soc Date: 2004-07-07 Impact factor: 15.419

9. Synthesis and evaluation of a mechanism-based inhibitor of KDO8P synthase.

Authors: Valery Belakhov; Ekaterina Dovgolevsky; Emilia Rabkin; Smadar Shulami; Yuval Shoham; Timor Baasov
Journal: Carbohydr Res Date: 2004-01-22 Impact factor: 2.104

10. Direct chemical synthesis of the beta-mannans: linear and block syntheses of the alternating beta-(1-->3)-beta-(1-->4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa.

Authors: David Crich; Wenju Li; Hongmei Li
Journal: J Am Chem Soc Date: 2004-11-24 Impact factor: 15.419

5 in total

1. Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.

Authors: Wei Huang; Qi Gao; Geert-Jan Boons
Journal: Chemistry Date: 2015-08-06 Impact factor: 5.236