16713-80-7

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C10H14O7/c1-5(11)16-8-7(6-2-12-3-13-6)17-10-9(8)14-4-15-10/h6-10H,2-4H2,1H3/t6-,7-,8+,9-,10+/m1/s1

Upstream product

• 78730-56-0 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt 
• 75-36-5 acetyl chloride 
• 141-78-6 ethyl acetate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 108-24-7 acetic anhydride 
• 77-76-9 2,2-dimethoxy-propane 
• 57-50-1 Sucrose 
• 50-99-7 D-glucose 
• 13964-22-2 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 581-55-5 benzylidene 1,1-diacetate 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-D-glucofuranoside 
• 79-20-9 acetic acid methyl ester 
• 99605-27-3 3-O-(tert-butyldimethylsilyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 7210-37-9 (R)-3-hydroxy-3-phenylbutyric acid methyl ester 
• 880-65-9 (-)S β-hydroxy β-phenyl n-butanoate de methyle 
• 102029-58-3 3-O-acetyl-6-O-benzoyl-1,2-O-isopropylidene-5-O-methylsulphonyl-α-D-glucofuranose 
• 52129-03-0 2,2-dimethyl-4-phenyl-1,3-dioxolane 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 20316-77-2 (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 20689-03-6 1-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 582-52-5 diacetone glucose 
• 10470-80-1 1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 
• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 29364-56-5 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 68095-73-8 3,5-Di-O-acetyl-1,2-O-isopropyliden-6-O-trityl-α-D-glucofuranose 

Relevant academic research and scientific papers

Thioglucose compound and preparation method thereof

The invention provides a thioglucose compound which has the following general formula: Wherein R is selected from H or acetyl. The preparation method of the thioglucose compound is easy to obtain, low in production cost and suitable for industrial product

Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols

Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.

Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition

The acylation of alcohols, phenols, amines, and thiophenols was accomplished with 0.5 mol % of tris(pentafluorophenyl)borane [B(C 6F5)3] at ambient temperature under solvent-free condition. Major advantages of this method include high yield, short reaction time, simple procedure, compatibility with sensitive protecting groups as well as other functional groups, absence of racemization of optical active compounds, and epimerization of sugars.

Synthesis of a novel bicyclic nucleoside with a 3,7-anhydrooctofuranosyl skeleton

We have developed an efficient route for the synthesis of a novel bicyclic nucleoside using a key intermediate 13, which was prepared from 1,2:5,6-di-O-isopropylidene-O-d-glucose. 1,2-Nucleophilic addition of aldehyde 8 with allyltrimethylsilane and intra

Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

An efficient synthesis of methyl 1,3-O-isopropylidene-α-D- fructofuranoside and 2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose

Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-d-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-d-gluc

Efficient acetylation of carbohydrates promoted by imidazole

An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

InCl3 as a powerful catalyst for the acetylation of carbohydrate alcohols under microwave irradiation

Indium(III) chloride catalyzed microwave assisted acetylation of different carbohydrates is an efficient synthesis of per-O-acetyl derivatives and provides the products in good to excellent yields.

Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species

(Chemical Equation Presented) Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride-MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-α-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O2-CBu t)2 between pivalic anhydride and MoO2Cl 2 as the catalyst.

Asymmetric synthesis of azetidin-2-ones by [2+2] cycloaddition using chiral imines derived from D-(+)-glucose

Asymmetric synthesis of β-lactams by the [2+2] cycloaddition of ketenes with chiral imines derived from D-(+)-glucose was carried out; predominantly cis-β-lactams were formed with very high diastereoselectivity. The stereochemistry at C-3 and C-4 was esta