6698-38-0

Usage

Molecular weight

424.56 g/mol

Structure

A tetrahydropyran ring with a benzyldisulfanyl group attached, and three acetyloxy and three acetoxy groups attached to the pyran ring.

Type

A triacetate derivative of a tetrahydropyran ring.

Usage

Commonly used in the synthesis of various organic compounds, as a reagent in chemical reactions, and as a fragrance ingredient in personal care products.

Precautions

Handle with care, as it may pose health hazards if not properly managed.

Upstream product

• 150-60-7 dibenzyl disulphide 
• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 19879-84-6 tetraacetyl thioglucose 
• 1318852-94-6 N-phthalyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide 
• 100-53-8 phenylmethanethiol 

Relevant academic research and scientific papers

Direct Synthesis of Unsymmetrical Glycosyl Disulfides from Glycosyl Bromides

A significantly fast one step reaction condition has been developed for the synthesis of unsymmetrical anomeric glycosyl disulfide derivatives in excellent yield by the treatment of anomeric glycosyl bromides with a combination of carbon disulfide (CS2) and sodium sulfide nonahydrate (Na2S ? 9H2O) in the presence of symmetrical alkyl, aryl and glycosyl disulfides at room temperature. Exclusive formation of anomerically beta-disulfides was observed under the reaction conditions. Most of the reactions are high yielding and suitable for scale-up synthesis.

Novel strategies for the synthesis of unsymmetrical glycosyl disulfides

Novel strategies for the efficient synthesis of unsymmetrical glycosyl disulfides are reported. Glycosyl disulfides are increasingly important as glycomimetics and molecular probes in glycobiology. Sialosyl disulfides are synthesised directly from the chlorosialoside Neu5Ac2Cl, proceeding via a thiol-disulfide exchange reaction between the sialosyl thiolate and symmetrical disulfides. This methodology was adapted and found to be successfully applicable to the synthesis of unsymmetrical glucosyl disulfides under mild conditions.

Synthesis of mixed glycosyl disulfides/selenenylsulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent

An easy and mild method has been developed for the synthesis of mixed glycosyl disulfides/selenenylsulfides from glycosyl halides and diaryl/dialkyl dichalcogenides in the presence of benzyltriethylammonium tetrathiomolybdate [(BnEt3N)2MoS4]. The salient feature of this method is the sulfur transfer from [BnEt3N]2MoS4 to form glycosyl disulfides which with excess tetrathiomolybdate further undergo exchange reaction with other dichalcogenides in a one-pot operation.

Glycosylation via mixed disulfide formation using glycosylthio-phthalimides and -succinimides as glycosylsulfenyl-transfer reagents

The silver salts of tetra-O-acetyl α- or -β-d-glycopyranosyl thiols 1a-4a react smoothly with N-bromophthalimide and N-bromosuccinimide to furnish glycosylthio-phthalimide (1b-4b) and -succinimide (1c-3c) derivatives. Reactions of these reagents with alip

Efficient one-pot synthesis of glycosyl disulfides

Methodology for the efficient and facile synthesis of glycosyl disulfides is reported. A one-pot procedure employing mild conditions using diethyl azodicarboxylate is described to synthesise a series of glycosyl disulfides in excellent yields.