3253-75-6

Usage

Uses

Used in Organic Synthesis:
a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate) is used as a building block for the synthesis of various compounds due to its protected hydroxyl functions and enhanced solubility and stability.
Used in Carbohydrate Chemistry:
a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate) is used as a key intermediate in the synthesis of complex natural products and pharmaceuticals, particularly in the field of carbohydrate chemistry.
Used in Pharmaceutical Industry:
a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-, 3-(4-methylbenzenesulfonate) is used as a starting material for the development of new pharmaceuticals, leveraging its unique structural features and reactivity in organic synthesis.

Upstream product

• 78730-56-0 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose potassium salt 
• 98-59-9 p-toluenesulfonyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 79378-71-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 92502-91-5 Sodium; (Z)-2-methyl-3-oxo-pent-1-en-1-olate 
• 50-99-7 D-glucose 
• 536-57-2 p-toluene sulfinic acid 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 2875-90-3 5,6-O-carbonyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 79378-73-7 1,2:5,6-Di-O-isopropyliden-3-O-(p-tolylsulfinyl)-α-D-allofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 2595-05-3 Diacetone D-glucose 

Downstream Products

• 17690-23-2 methyl-[O²,O⁴,O⁶-triacetyl-O³-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 17460-41-2 methyl-[O²,O⁴,O⁶-triacetyl-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 2774-28-9 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 50705-39-0 O³-(toluene-4-sulfonyl)-D-glucose 
• 2946-01-2 (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 83049-98-3 2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl bromide 
• 911650-76-5 methyl-[O²,O⁴,O⁶-trimethyl-O³-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 911650-81-2 methyl-[O²,O⁴,O⁶-trimethyl-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 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 
• 4005-35-0 3-Desoxy-D-galaktose 
• 2774-29-0 (3aR,5R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 

Relevant academic research and scientific papers

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

Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.

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.

Monosaccharide Derivatives as Anti-Inflammatory and/or Anti-Cancer Agents

The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su

MONOSACCHARIDE DERIVATIVES

The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su

MONOSACCHARIDE DERIVATIVES

The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases s

Monosaccharide derivatives

The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases s

MONOSACCHARIDE DERIVATIVES AS ANTI-INFLAMMATORY AND/OR ANTI-CANCER AGENTS

The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su

MONOSACCHARIDE DERIVATIVES AS ANTI-INFLAMMATORY AND/OR ANTI-CANCER AGENTS

The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su