10470-80-1

Basic information

• Product Name: 5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-5-thio-D-glucopyranose;5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate;1,2,3,4,6-O-pentaacetyl-5-deoxy-5-thio-D-glucopyranose;RFPPVTQRDZKNPS-IWQYDBTJSA-N
• CAS NO: 10470-80-1
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 406.40488
• Mol File: 10470-80-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate(10470-80-1)
• EPA Substance Registry System: 5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate(10470-80-1)

Safety Data

• Hazardous Substances Data: 10470-80-1(Hazardous Substances Data)

Usage

Description

5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate is a chemical compound derived from D-glucopyranose, a common sugar molecule, featuring a thioether linkage with a sulfur atom bonded to a carbon atom. As a pentaacetate, it has five acetyl groups attached to the sugar, which may confer unique properties and reactivity. This versatile compound holds potential in organic synthesis and as a building block for the creation of other compounds, making it a valuable tool in chemistry and biochemistry.

Uses

Used in Organic Synthesis:
5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for selective reactions and modifications, facilitating the synthesis of complex molecules with specific properties.
Used in Biochemistry Research:
In biochemistry, 5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate is used as a building block for the development of novel bioactive molecules. Its ability to be modified and incorporated into larger structures makes it a promising candidate for the design of new pharmaceuticals and biological probes.
Used in Pharmaceutical Industry:
5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate is used as a key component in the synthesis of pharmaceuticals, particularly those targeting specific biological pathways or receptors. Its unique chemical properties may contribute to the development of drugs with improved efficacy and selectivity.
Used in Material Science:
In material science, 5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate is used as a component in the development of new materials with tailored properties. Its ability to form stable linkages and interact with other molecules can lead to the creation of materials with specific applications, such as sensors or drug delivery systems.
Used in Analytical Chemistry:
5-Thio-D-glucopyranose 1,2,3,4,6-pentaacetate is used as a reagent or standard in analytical chemistry for the detection, quantification, or characterization of other compounds. Its distinct chemical properties may provide a basis for the development of new analytical methods or the improvement of existing ones.

Upstream product

• 10579-05-2 Methyl-D-glucothiapyranosid 
• 108-24-7 acetic anhydride 
• 37614-79-2 5,6-anhydro-5,6-epithio-1,2-O-isopropylidene-α-D-glucofuranose 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 102029-58-3 3-O-acetyl-6-O-benzoyl-1,2-O-isopropylidene-5-O-methylsulphonyl-α-D-glucofuranose 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 10227-17-5 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 627466-64-2 2,3,4,6-tetra-O-benzoyl-D-glucopyranose 

Downstream Products

• 10227-18-6 1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside 
• 161687-19-0 allyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 1053624-48-8 (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-thiopyran-3,4,5-triol 
• 146558-09-0 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 146558-10-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-5'-thio-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 146609-14-5 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester 
• 146558-07-8 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 146558-08-9 3,4,6-tri-O-acetyl-1,2-(methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-2-yl)-α-D-5'-thio-α-D-glucopyranose orthoacetate 
• 606968-07-4 methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzoyl-5-thio-α-D-mannopyranoside 
• 211509-30-7 methyl 3-O-(2,3,4,6-tetra-O-acetyl-5-thio-α-D-glucopyranosyl)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 161687-11-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-5-thio-β-D-glucopyranoside 
• 161687-10-1 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-5-thio-α-D-glucopyranoside 

Relevant articles and documents

Radical-mediated bromination of peracetylated 5-thio-D-xylopyranosyl bromides: An easy access to the corresponding anomeric orthothiolactones

On treatment with N-bromosuccinimide in refluxing carbon tetrachloride under irradiation with visible light, both α and β anomers of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide were converted mainly to 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosylidene dibromide (5) and to 2,3,4-tri-O-acetyl-5(S)-5-bromo-5-thio-D-xylopyranosylidene dibromide (6). Whereas the more reactive β anomer could be transformed cleanly into the dibromide 5 after heating for 2 h, complete conversion of the α-bromide required a prolonged treatment (~ 5 h) leading to a mixture of di-, tri- and tetra-bromides. Similarly, an anomeric mixture of 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranosyl bromide yielded mainly tribromide 11 after prolonged heating. The reaction rates and the structure of the products showed again the higher reactivity of axial C-H bonds at either C-1 or C-5 in pyranosyl rings towards S(H)2 processes. However, activation by the sulfur atom allowed attack of equatorial bonds as well and polybromination at both C-1 and C-5. Treatment of the C-1 dibromide 5 by silver triflate in the presence of either alcohols or thiols yielded the corresponding 5-thiosugar ortholactones 12-15. Methyl 1-methoxy-5-thio-D-xylopyranoside (18), obtained from 12 on deacetylation, showed no venous antithrombotic activity in rats according to a Wessler test.

Synthesis and Evaluation of 1,5-Dithia- d -laminaribiose, Triose, and Tetraose as Truncated β-(1→3)-Glucan Mimetics

The preparation and characterization of a series of di-, tri-, and tetrasaccharide analogues of β-(1→3)-glucans is described in which each pyranoside ring is replaced by a 5-thiopyranosyl ring and each glycosidic oxygen by a thioether. These oligomeric 1,

Chemical-enzymatic synthesis of 5′-thio-N-acetyllactosamine: The first disaccharide with sulfur in the ring of the nonreducing sugar

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