3253-75-6

Basic information

• Product Name: a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate)
• Synonyms: Glucofuranose,1,2:5,6-di-O-isopropylidene-, p-toluenesulfonate (6CI); Glucofuranose,1,2:5,6-di-O-isopropylidene-, p-toluenesulfonate, a-D- (7CI,8CI); a-D-Glucofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-,4-methylbenzenesulfonate (9CI); Furo[2,3-d]-1,3-dioxole, a-D-glucofuranose deriv.;1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose 3-p-toluenesulfonate; NSC 14163
• CAS NO: 3253-75-6
• Molecular Formula: C19H26 O8 S
• Molecular Weight: 414.477
• Mol File: 3253-75-6.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate)(3253-75-6)
• EPA Substance Registry System: a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate)(3253-75-6)

Safety Data

• Hazardous Substances Data: 3253-75-6(Hazardous Substances Data)

Usage

General Description

This chemical, also known as α-D-Glucofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate), is a derivative of α-D-glucose. It is commonly used in organic synthesis and as a building block in the production of various compounds. The 1,2:5,6-bis-O-(1-methylethylidene) group serves to protect the hydroxyl functions of the glucose, while the 4-methylbenzenesulfonate moiety enhances solubility and stability. a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate) is often employed in the field of carbohydrate chemistry and can be used in the synthesis of complex natural products and pharmaceuticals.

Upstream product

• 78730-56-0 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt 
• 98-59-9 p-toluenesulfonyl chloride 
• 79378-71-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 582-52-5 (3aR,5S,6S,6aR)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 536-57-2 p-toluene sulfinic acid 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 2595-05-3 Diacetone D-glucose 
• 79378-73-7 1,2:5,6-Di-O-isopropyliden-3-O-(p-tolylsulfinyl)-α-D-allofuranose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 2875-90-3 5,6-O-carbonyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 50-99-7 D-glucose 

Downstream Products

• 141903-84-6 3-((4-methoxyphenyl)telluro)-3-deoxy-1,2:5,6-di-O-isopropylidene-D-glucofuranose 
• 145125-27-5 Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 81159-66-2 3-deoxy-3-C-(phenylphosphino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 21870-78-0 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 2774-28-9 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 7702-25-2 3-O-p-toluenesulfonyl-D-glucopyranose 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 685142-64-7 (-)-(2R,4R,5R)-methyl 4-(4-methoxybenzyloxy)-5-methoxytetrahydrofuran-2-carboxylate 
• 685142-66-9 (2S,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester 
• 685142-67-0 (2R,4R,5R)-2-Hydroxymethyl-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester 
• 15919-16-1 5-β-formyl-4-β-O-tosyl-2α,3α-O-isopropylidenetetrahydrofuran 
• 43138-33-6 5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran 
• 7508-81-8 [(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 

Relevant articles and documents

Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation

N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NM

C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies

To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.

Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium

In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.