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

General Description

1-deoxy-D-glucose tetraacetate is a chemical compound that belongs to the family of glucose derivatives. It is a synthetic compound and is commonly used in biochemical research as a non-metabolizable analog of glucose. The presence of four acetyl groups in the compound increases its lipophilicity and stability, making it a useful tool for studying glucose metabolism and transport in cells. Additionally, 1-deoxy-D-glucose tetraacetate has also been investigated for its potential anti-cancer properties, as it has been shown to inhibit glycolysis and cell proliferation in cancer cells. Its unique structure and non-metabolizable nature make it a valuable compound for various biochemical and pharmacological studies.

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 100351-75-5 2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 
• 10300-83-1 O²,O³,O⁴,O⁶-Tetraacetyl-O¹-nitro-α-D-glucopyranose 
• 108-94-1 cyclohexanone 
• 108-24-7 acetic anhydride 
• 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 
• 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

• 154-58-5 1,5-anhydro-D-glucitol 
• 65371-07-5 2,3-di-O-p-tolylsulphonyl-4,6-O-benzylidene-1,5-anhydro-D-glucitol 
• 65391-44-8 1,5-anhydro-4,6-O-(R)-benzylidene-D-glucitol 
• 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 
• 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 

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.

Development of a catalytic cycle for the generation of C1-glycosyl carbanions with Cp2TiCl2: Application to glycal synthesis

A catalytic cycle has been developed for the conversion of glycosyl halides to their corresponding glycals using Cp2TiCl2. This process can be effectively used with only 30% of the in situ generated single electron reducing agent in contrast to the 2 equivalents normally employed. (C) 2000 Published by Elsevier Science Ltd.

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.