10227-18-6

Basic information

• Product Name: PENTAACETYL-5-THIOGLUCOSE
• Synonyms: PENTAACETYL-5-THIOGLUCOSE
• CAS NO: 10227-18-6
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 406.40488
• Mol File: 10227-18-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PENTAACETYL-5-THIOGLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAACETYL-5-THIOGLUCOSE(10227-18-6)
• EPA Substance Registry System: PENTAACETYL-5-THIOGLUCOSE(10227-18-6)

Safety Data

• Hazardous Substances Data: 10227-18-6(Hazardous Substances Data)

Usage

General Description

Pentaacetyl-5-thioglucose is a chemical compound that is derived from glucose, a simple sugar. It is a synthetic derivative that has five acetyl groups attached to the thiol group of the glucose molecule. The thiol group, also known as a sulfhydryl group, consists of a sulfur atom bonded to a hydrogen atom and is typically found in organic compounds. Pentaacetyl-5-thioglucose is commonly used in organic chemistry and biochemical research as a reagent and building block for the synthesis of various compounds. It has also been studied for its potential pharmaceutical and medical applications, particularly in the development of new drugs.

Upstream product

• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 108-24-7 acetic anhydride 
• 153053-29-3 phenyl 2,3,4,6-tetra-O-acetyl-1,5-dithio-β-D-glucopyranoside 
• 176213-92-6 1,6-anhydro-2-azido-3-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 10470-80-1 1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 
• 84039-44-1 2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl bromide 
• 84039-45-2 2,3,4,6-tetra-O-acetyl-5-thio-β-D-glucopyranosyl bromide 

Downstream Products

• 131757-93-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-5-thio-α-D-glucopyranose 
• 131757-84-1 methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside 
• 131757-92-1 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one 
• 131757-87-4 5-(benzyloxymethyl)-thiophene-2-carboxaldehyde 
• 85446-67-9 5-thio-D-glucal 
• 260360-92-7 p-trifluoromethyl-N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosylamine 
• 260360-93-8 p-trifluoromethyl-N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-β-D-glucopyranosylamine 
• 260360-90-5 p-nitro-N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosylamine 
• 260360-91-6 p-nitro-N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-β-D-glucopyranosylamine 
• 260360-86-9 p-methoxy-N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosylamine 
• 260360-87-0 p-methoxy-N-phenyl 2,3,4,6-tetra-O-acetyl-thio-β-D-glucopyranosylamine 
• 260360-88-1 N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosylamine 

Relevant articles and documents

A novel 5-thioglycosylation method with 1,5-dithioglycosyl donors: relevance to exo- versus endocyclic activation

5-Thioglucosylation of a 1,6-anhydro-2-azido-2-deoxy-β-d-glucopyranose derivative was carried out with various 1,5-dithioglucosyl donors. The use of per-O-acetyl donors resulted in poor yields of an α-disaccharide. On the other hand, per-O-benzyl donors s

SYNTHESIS OF 1,5-DITHIO-D-GLUCOPYRANOSE AND SOME OF ITS BIOLOGICALLY RELEVANT DERIVATIVES.

5-Thio-D-glucose was transformed into 1,5-dithio analog 5 through a sequence involving anomeric bromination followed by a Cerny hydrosulfurization reaction.The nucleophilic reactivity of this first representative of a new class of sugar mercaptans was inv