13137-69-4

Basic information

• Product Name: 1-deoxy-D-glucose tetraacetate
• Synonyms: 1-deoxy-D-glucose tetraacetate
• CAS NO: 13137-69-4
• Molecular Weight: 332.307
• Mol File: 13137-69-4.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 1-deoxy-D-glucose tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxy-D-glucose tetraacetate(13137-69-4)
• EPA Substance Registry System: 1-deoxy-D-glucose tetraacetate(13137-69-4)

Safety Data

• Hazardous Substances Data: 13137-69-4(Hazardous Substances Data)

Usage

Description

1-deoxy-D-glucose tetraacetate is a synthetic glucose derivative belonging to the family of glucose analogs. It is characterized by the presence of four acetyl groups, which enhance its lipophilicity and stability. 1-deoxy-D-glucose tetraacetate is commonly utilized in biochemical research as a non-metabolizable analog of glucose, making it a valuable tool for studying glucose metabolism and transport in cells. Furthermore, 1-deoxy-D-glucose tetraacetate has been investigated for its potential anti-cancer properties, as it has demonstrated the ability to inhibit glycolysis and cell proliferation in cancer cells.

Uses

Used in Biochemical Research:
1-deoxy-D-glucose tetraacetate is used as a research tool for studying glucose metabolism and transport in cells due to its non-metabolizable nature and increased lipophilicity.
Used in Pharmaceutical Research:
1-deoxy-D-glucose tetraacetate is used as a potential anti-cancer agent for its ability to inhibit glycolysis and cell proliferation in cancer cells, making it a candidate for further investigation in oncology.
Used in Drug Development:
1-deoxy-D-glucose tetraacetate is utilized in the development of pharmaceuticals targeting cancer treatment, given its potential to disrupt key metabolic pathways in cancer cells and its non-metabolizable properties, which may contribute to increased efficacy and reduced side effects.

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4851-64-3 phosphoric acid diethyl ester vinyl ester 
• 112290-59-2 2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride 
• 108-94-1 cyclohexanone 
• 108-24-7 acetic anhydride 
• 10300-83-1 O²,O³,O⁴,O⁶-Tetraacetyl-O¹-nitro-α-D-glucopyranose 
• 100351-75-5 2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 
• 141665-73-8 Fmoc-ΔAla-OBzl 
• 134160-51-3 (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one 
• 59524-07-1 N-(Benxyloxycarbonyl)dehydroalanine benzyl ester 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 107-13-1 acrylonitrile 
• 99756-38-4 methyl hepta-O-diethylboryl-β-maltoside 

Downstream Products

• 65190-39-8 (4aR,7S,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 
• 89873-05-2 1,5-Anhydro-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-D-ribo-hexitol 
• 89873-03-0 1,5-Anhydro-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-D-ribo-3-ulohexitol 
• 89872-98-0 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol 
• 89872-97-9 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol 
• 89872-96-8 1,5-Anhydro-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-D-glucitol 
• 89873-02-9 1,5-Anhydro-4,6-O-benzylidene-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-D-glucitol 2,3-Lactol 
• 89873-08-5 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol 
• 65391-44-8 1,5-anhydro-4,6-O-(R)-benzylidene-D-glucitol 
• 65371-07-5 2,3-di-O-p-tolylsulphonyl-4,6-O-benzylidene-1,5-anhydro-D-glucitol 
• 161344-98-5 4,5-anhydro-4,6-O-benzylidene-2-(2-amino-6-chloropurin-9-yl)-2,3-dideoxy-D-arabino-hexitol 
• 152613-21-3 1,5-anhydro-4,6-O-benzylidene-2-(adenin-9-yl)-2,3-dideoxy-D-arabino-hexitol 
• 156715-24-1 1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-(p-tolylsulfonyl)-D-ribo-hexitol 
• 152613-23-5 5-Iodo-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Reactivity of glucosyl radical in the presence of phenols

Glucosyl radicals from the photoreaction of α-bromo-2,3,4,6-tetra-O-acetylglucose (ABG) with hexabutylditin react with phenols. 4-H3-COC6H4O· was identified by means of EPR spectroscopy in the case of 4-methoxyphenol, and the corresponding α-O-glucoside was isolated along with 1- and 2-deoxysugars and the dimers of glucosyl radical. The present results are consistent with the formation of α-O-glucosides observed in the electrochemical reaction of ABG and phenols, although in this case the dimers represent the main reaction products.

NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: A tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD 4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose were achieved upon heating to 80 C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (d-galacto), but some (d-manno, 5-thio-d-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light.

Synthesis of 1,2-trans C-glycosyl compounds by reductive samariation of glycosyl iodides

Reductive samariation of per-O-trimethylsilyl or benzyl glycopyranosyl iodides in the presence of carbonyl compounds provides the corresponding 1,2-trans-C-glycosyl compounds in good yields.

Radical dimerization of glycosyl 2-pyridylsulfones with samarium (II) iodide in the presence of HMPA

Reduction of glycosyl 2-pyridylsulfones by samarium (II) iodide in the presence of HMPA leads to glycosyl dimers in up to 74% yield. This is rationalized by a free-radical mechanism.