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

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

Uses

Used in Organic Chemistry:
PENTAACETYL-5-THIOGLUCOSE is used as a reagent in organic chemistry for its ability to facilitate the synthesis of a range of organic compounds. Its unique structure with acetyl groups attached to the thiol group of the glucose molecule makes it a versatile building block in chemical reactions.
Used in Biochemical Research:
In biochemical research, PENTAACETYL-5-THIOGLUCOSE serves as a valuable building block for the synthesis of biologically active molecules. Its properties allow it to be incorporated into complex biochemical structures, contributing to the development of new compounds with potential therapeutic effects.
Used in Pharmaceutical Development:
PENTAACETYL-5-THIOGLUCOSE is used as a precursor in the development of new pharmaceuticals. Its potential applications in medicine have been explored, and ongoing research aims to harness its properties to create novel drugs with improved efficacy and safety profiles.
Used in Medical Applications:
In the medical field, PENTAACETYL-5-THIOGLUCOSE is studied for its potential use in the treatment of various conditions. Its unique chemical structure may offer new avenues for therapeutic intervention, and ongoing research is focused on understanding its mechanisms of action and potential benefits in clinical settings.

Upstream product

• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 108-24-7 acetic anhydride 
• 10470-80-1 1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 
• 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 
• 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 
• 260360-89-2 N-phenyl 2,3,4,6-tetra-O-acetyl-5-thio-β-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

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.

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