Novel strategies for the synthesis of unsymmetrical glycosyl disulfides.

Efficient synthesis of unsymmetrical disulfides

A novel way of synthesizing unsymmetrical disulfides from thiols with DDQ is presented here. This procedure ran in a straightforward manner to give high product yields. Unsymmetrical disulfides were directly synthesized from the corresponding mixture of thiols in equimolar amounts under mild conditions. 2011 Elsevier Ltd. All rights reserved.

Synthesis of Unsymmetrical Ethers Catalysed by Polyvinyl Sulfuric Acid & PVSA / Nano RH SiO2 as a Novel Solid Acid Nanocomposite

The methodology involves preparing polyvinyl sulfuric acid as a solid acid by simple mixing ofpolyvinyl alcohol with chlorosulfonic acid in CH2Cl2 at room temperature. The catalytic ability ofthe solid acid was investigated for the facile conversion of benzylic alcohols to the unsymmetricalethers with aliphatic alcohols in the presence of the solid acid. Results show that the solid acid isan ap...

Glycosyl disulfides: novel glycosylating reagents with flexible aglycon alteration.

[reaction: see text] Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nat...

Convenient method for the synthesis of symmetrical disulfides using 1-butyl- 3-methylimidazolium hydroxide in water

A coordinated synthesis and conjugation strategy for the preparation of homogeneous glycoconjugate vaccine candidates.

Glycoconjugates are the center of many therapeutic strategies and carbohydrate-based vaccines in particular hold great promise. The development of glycovaccines, however, can be hindered by the limited access offered by natural sources to homogeneous antigenic carbohydrates; efficient chemical synthesis offers an attractive route to pure samples of these carbohydrates. Furthermore, for an optim...