6612-79-9

Basic information

• Product Name: .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate
• Synonyms: .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate
• CAS NO: 6612-79-9
• Molecular Formula: C₂₀H₂₄O₉S₂
• Molecular Weight: 472.52916
• Mol File: 6612-79-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 117-118 °C(Solv: methanol (67-56-1))
• Boiling Point: 532.9°Cat760mmHg
• Flash Point: 256.9°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 1.95E-11mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate(6612-79-9)
• EPA Substance Registry System: .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate(6612-79-9)

Safety Data

• Hazardous Substances Data: 6612-79-9(Hazardous Substances Data)

Usage

General Description

.beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)-, tetraacetate is a chemical compound that consists of a glucopyranose ring with a phenyl dithioether group attached in place of the hydroxyl group at the first carbon. It is tetraacetylated, meaning that each hydroxyl group on the glucose ring is esterified with an acetyl group. This chemical has potential applications in organic synthesis and can be used as a reagent in chemical reactions to introduce the phenyldithio group to other compounds. Additionally, it may be used as a building block in the synthesis of more complex organic molecules. The tetraacetate form of .beta.-D-Glucopyranose, 1-deoxy-1-(phenyldithio)- is important in controlling the reactivity and properties of the compound for specific applications.

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 
• 1318852-98-0 2,3,4,6-tetra-O-acetyl-1-S-(pyrrolidine-2,5-dione)-1-thio-β-D-glucopyranoside 
• 1318852-94-6 N-phthalyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide 
• 882-33-7 diphenyldisulfane 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 

Relevant articles and documents

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.

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.

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