28713-39-5

Usage

Uses

Used in Pharmaceutical Industry:
3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose is used as an impurity in the vasoprotective drug Tribenoside (T945630) for the treatment of hemorrhoids. Its presence in the drug contributes to mild anti-inflammatory and wound healing properties, making it a valuable component in the formulation of this medication.
Used in Chemical Research:
3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose can also be utilized in chemical research for the synthesis of various complex organic molecules and pharmaceuticals. Its unique structure allows for further functionalization and modification, making it a versatile building block in the development of new drugs and other chemical products.

Upstream product

• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 101996-88-7 3-O-benzyl-5-C-(2-furyl)-1,2-O-isopropylidene-α-D-glucopentofuranose 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 65462-15-9 3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose 
• 881993-91-5 3-O-benzyl-6-O-(1-methoxy-1-methylethyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 246162-52-7 6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 182298-39-1 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose N,N-butylenehydrazone 
• 100-44-7 benzyl chloride 
• 115243-95-3 (S)-Benzyloxy-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde 
• 182298-29-9 (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-[(E)-pyrrolidin-1-ylimino]-ethanol 

Downstream Products

• 115243-95-3 (S)-Benzyloxy-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde 
• 881993-93-7 6-O-(2-methylpropanoyl)-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 881993-92-6 6-O-butanoyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 138638-98-9 3,5-Di-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-6-C-methyl-α-D-gluco-hept-6-eno-1,4-furanose 
• 138638-95-6 Methyl (3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuran)uronate 
• 138638-97-8 3,5-Di-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-6-C-methylene-7-C-trimethylsilyl-α-D-gluco-hepto-1,4-furanose 
• 138638-96-7 3,5-Di-O-benzyl-1,2-O-isopropylidene-6-bis-C-<(trimethylsilyl)methyl>-α-D-glucofuranose 
• 138639-03-9 11,13-Di-O-acetyl-8,12-anhydro-3,5-di-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-6-C-methylene-D-ribo-α-D-gluco-trideca-9-eno-1,4-furanose 
• 162179-07-9 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose 
• 125161-48-0 6-O-Butanoyl-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Preparation and biological evaluation of some 1,2-O-isopropylidene-D- hexofuranose esters

The synthesis and biological evaluation of some new glycose esters bearing the 1,2-O-isopropylidene-D-hexofuranose functionality and belonging to the 3-O-acyl-D-allose and 6-O-acyl-D-glucose series are reported. When the results concerning cell growth inh

Stereoselective nucleophilic formylation and cyanation of α-alkoxy- and α-aminoaldehydes

The spontaneous 1,2-addition of formaldehyde N,N-dialkylhydrazones to carbohydrate-derived α-alkoxyaldehydes takes place under neutral conditions and in the absence of catalysts or promoters to afford the corresponding α-hydroxyhydrazones in good to excellent yields and with highly anti diastereoselectivities. Subsequent transformations of the hydrazono group into aldehydes and nitriles following known procedures provide a new entry into the homologation of carbohydrates and the synthesis of cyanohydrins, respectively. Additionally, reaction of methyleneaminopyrrolidine with N-Boc-protected α-aminoaldehydes from natural amino acids efficiently affords the corresponding adducts under the same conditions. From these adducts, a variety of biologically interesting α-hydroxy-β-aminocarbonyl compounds can be accessed upon manipulation of the hydrazone moiety.

Glycosylation with 1,2-anhydromannofuranose benzyl ether as the glycosyl donor: A comparison between sugar pyranose and furanose acceptors for thelr primary hydroxy activity

Some 1→5 and 1→6 α-linked furano-disaccharide derivatives were synthesized using 1,2-anhydromannofiiranose as the glycosyl donor. Comparison of the glycosyl acceptors indicated that the activity of primary hydroxyl groups of glycofuranoses was much lower than that of glycopyranoses.

Lewis Acid-Catalyzed Deprotection of p-Methoxybenzyl Ether

The p-methoxybenzyl protecting group was readily removed from alcohols and phenols using catalytic amounts of AlCl3 or SnCl2 · 2H2O in the presence of EtSH at room temperature. Under these mild conditions other protecting groups such as methyl and benzyl ethers, p-nitrobenzoyl esters, TBDPS ethers and isopropylidene acetal were unchanged.

Stereospecific addition of formaldehyde dialkylhydrazones to sugar aldehydes. Synthesis of cyanohydrins and α-hydroxy aldehydes

Formaldehyde dialkylhydrazones smoothly add to sugar aldehydes without any need of promoter or catalyst. α-Hydroxy dialkylhydrazones, which are obtained in good yields and high stereoselectivities, have been successfully transformed in cyanohydrins by treatment with magnesium monoperoxyphtalate (MMPP) and in O-protected α-hydroxy aldehydes by ozonolysis or HCl mediated hydrolysis. No racemization was observed in the cleavage of the dialkylhydrazone group.

Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions

The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the

A convenient preparation of 5-benzyl ethers of D-gluco- and D-manno-furanose derivatives

Keywords: Glucofuranose; Mannofuranose; Selective benzylation; Two-phase benzylation

Synthesis of the antibiotic 1,5-dideoxy-1,5-imino-D-glucitol; concomitant formation of the D-mannitol analogue

The easy accessible 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose was converted in six steps into 1,2-O-isopropylidene-3,6-di-O-benzyl-5-deoxy-5-azido-α-D-glucofuranose.The latter afforded, after acidolysis followed by hydrogenolysis, 1-deoxynojirimicine and a small quantity of 1-deoxymannonojirimicine.The antibiotic thus obtained had an inhibitory effect on the trimming of N-linked carbohydrates in IgM.