6612-79-9

Usage

Uses

Used in Organic Synthesis:
.beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate is used as a reagent in organic synthesis for introducing the phenyldithio group to other compounds. This application is valuable for creating a variety of complex organic molecules with specific functional groups.
Used in Chemical Reactions:
.beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate is used as a building block in the synthesis of more complex organic molecules. Its tetraacetate form is particularly important for controlling the reactivity and properties of the compound, making it suitable for specific applications in chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate may be used as a key intermediate in the development of new drugs, particularly those targeting carbohydrate-based interactions or requiring the phenyldithio group for biological activity.
Used in Research and Development:
.beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate can be employed in research and development settings to study the effects of the phenyldithio group on the chemical and biological properties of various molecules, potentially leading to advancements in the understanding of molecular interactions and the design of novel therapeutic agents.

InChI:InChI=1/C20H24O9S2/c1-11(21)25-10-16-17(26-12(2)22)18(27-13(3)23)19(28-14(4)24)20(29-16)31-30-15-8-6-5-7-9-15/h5-9,16-20H,10H2,1-4H3

Upstream product

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 931-59-9 benzenesulfenyl chloride 
• 19879-84-6 tetraacetyl thioglucose 
• 108-98-5 thiophenol 
• 17665-58-6 benzenesulfinyl-acetonitrile 
• 882-33-7 diphenyldisulfane 
• 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 
• 1318852-94-6 N-phthalyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide 
• 1318852-98-0 2,3,4,6-tetra-O-acetyl-1-S-(pyrrolidine-2,5-dione)-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

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 synthesis of unsymmetrical disulfides through sulfenic acids

Unsymmetrical disulfides, some of which are biologically interesting, were prepared by the in situ generation of sulfenic acids from suitable sulfinyl precursors and their coupling with various thiols. This methodology represents an efficient and mild procedure to obtain disulfides in excellent yields. It allows the presence of base/acid and/or thermolabile functional groups in both the sulfenic acid and the thiol on the basis of the choice of suitable sulfenic acid precursors and offers wide chances of modulating the construction of the disulfide bridge between different structural skeletons such as homo- and heteroaromatic, amino acidic and sugar residues. Wiley-VCH Verlag GmbH & Co. KGaA.