13137-69-4

Usage

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

• 108-24-7 acetic anhydride 
• 83823-00-1 C₄₄H₉₄B₈O₁₁ 
• 83823-00-1 C₄₄H₉₄B₈O₁₁ 
• 99756-41-9 benzyl hepta-O-diethylboryl-β-lactoside 
• 99756-38-4 methyl hepta-O-diethylboryl-β-maltoside 
• 112290-59-2 2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride 
• 107-13-1 acrylonitrile 
• 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 
• 59524-07-1 N-(Benxyloxycarbonyl)dehydroalanine benzyl ester 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 134160-51-3 (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one 
• 141665-73-8 Fmoc-ΔAla-OBzl 
• 100351-75-5 2-(Tetraacetyl-1-β-D-glucosylsulfonyl)-pyridin 

Downstream Products

• 154-58-5 1,5-anhydro-D-glucitol 
• 912847-96-2 2,6-anhydro-3,4,5-tri-O-benzyl-L-glucose 
• 912848-00-1 2-((2,3,4-tri-O-benzyl-β-D-xylopyranosyl)methyl)naphthalene 
• 13121-49-8 C-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-methanol 
• 78890-68-3 1-deoxy-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 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 

Relevant academic research and scientific papers

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.

REDUCTION STEREOSELECTIVE D'HALOGENURES DE GLYCOSYLES PAR LE DEUTERIEURE DE TRIBUTYLETAIN

The reduction of several glycosyl halides by tributyltin deuteride is shown to proceed with a high stereoselectivity, favouring α-attack.

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.

Towards α- or β-D-C-glycosyl compounds by tin-catalyzed addition of glycosyl radicals to acrylonitrile and vinylphosphonate, and flexible reduction of tetra-O-acetyl-α-D-glucopyranosyl bromide with cyanoborohydride

Photo-induced radical addition of acetylated α-D-glucopyranosyl bromide (1) to acrylonitrile or diethyl vinylphosphonate, in the presence of catalytic amounts of tri-n-butyltin chloride and sodium (or tetra-n-butylammonium) cyanoborohydride in excess, all

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.

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.

Zinc-N-base mediated synthesis of pyranoid glycals mechanistic studies

Reactions of acetobromoglucose 1 or acetylated 1-bromo-D-galactopyranosyl cyanide 3 with zinc dust in the presence of a N-base (1-methylimidazole, 4-methylpyridine, or triethylamine, pyridine, respectively) in ethyl acetate or benzene were efficiently inhibited by 10-30 mol % of 1,4-dinitrobenzene, elemental sulfur, or carbon tetrachloride. Presence of glycosyl radicals in these reactions was also shown by trapping them with tert-dodecyl mercaptan or methyl acrylate. Based on these observations and the high yielding formation of glycal derivatives 2 and 4 of high purity a free radical chain mechanism is proposed for the transformations.

Synthesis of α-(1->2)-, α-(1->3)-, α-(1->4)-, and α-(1->5)-C-Linked Disaccharides through 2,3,4,6-Tetra-O-acetylglucopyranosyl Radical Additions to 3-Methylidene-7-oxabicycloheptan-2-one Derivatives

The "naked sugar" (+)-1 (1R,2S,4R)-2-cyano-7-oxabicyclohept-5-en-2-yl (1S')-camphanate) has been converted into (+)-(1R,4R,5R,6R)-3-methylidene-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicycloheptan-2-one ((+)-3) and (-)-(1S,4R,5R,6R)-5-exo-(b

Free radical-mediated addition of peracetylated 1-bromo-β-D-glucopyranosyl chloride to acrylonitrile

Dropwise addition of a benzene solution of tri-n-butylstannane to a solution of 2,3,4,6-tetra-O-acetyl-1-bromo-β-D-glucopyranosyl chloride in boiling benzene containing acrylonitrile in excess led predominantly, under photolytic conditions, to a mixture of nonononitriles, either chlorinated or unsaturated. Dropwise addition of a benzene solution of tri-n butylstannane to a solution of 2,3,4,6-tetra-O- acetyl-1-bromo-β-D-glucopyranosyl chloride in boiling benzene containing acrylonitrile in excess led predominantly, under photolytic conditions, to a mixture of nonononitriles, either chlorinated or unsaturated.