19131-06-7

Usage

Uses

1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose is used as a synthetic intermediate for the production of various organic compounds.
Used in Pharmaceutical Industry:
1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose is used as a key component in the synthesis of pharmaceutical compounds, particularly those with potential therapeutic applications. Its unique structure allows for the development of novel drugs with improved efficacy and selectivity.
Used in Chemical Research:
1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose is used as a research tool in the field of organic chemistry, enabling scientists to explore new reaction pathways and develop innovative synthetic strategies.
Used in Material Science:
1,2:5,6-Di-O-isopropylidene-3-O-tosyl-α-D-gulofuranose is used as a building block for the development of new materials with unique properties, such as improved mechanical strength, thermal stability, or biocompatibility.

Upstream product

• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 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 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 536-57-2 p-toluene sulfinic acid 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 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 

Downstream Products

• 141903-84-6 3-((4-methoxyphenyl)telluro)-3-deoxy-1,2:5,6-di-O-isopropylidene-D-glucofuranose 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 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 
• 214918-32-8 [(3aR,5S,6S,6aR)-5-((R)-1-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 37073-89-5 [(3aR,5S,6S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 214918-31-7 [(3aR,5S,6S,6aR)-5-((S)-1-Hydroxy-2-iodo-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 451505-53-6 Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-benzyloxycarbonylamino-6-methyl-tetrahydro-pyran-3-yl ester 
• 451505-46-7 Toluene-4-sulfonic acid (R)-2-((3aR,5S,6S,6aR)-6-benzyloxycarbonylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester 
• 214918-34-0 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 16848-19-4 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 99042-38-3 1-(2,4-dinitrophenyl)-3-<(S)-2,3-O-isopropylidenedihydroxypropyl>pyrazole 
• 99042-39-4 1-(2,4-dinitrophenyl)-3-<(S)-2,3-di-O-acetyldihydroxypropyl>pyrazole 
• 99042-40-7 1-(2,4-dinitrophenyl)-3-<(S)-2,3-di-O-acetyldihydroxypropyl>-4-nitropyrazole 
• 28251-83-4 1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose 

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

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

N-azole substituted carbohydrates. Synthesis and transformations of 1- (3'-deoxy-1',2':5',6'-di-O-isopropylidene-α-D-glucofuranos-3'-yl)-azole derivatives

The synthesis and chemical manipulation of some 1-(3'-deoxy-1',2':5',6'- di-O-isopropylidene-α-D-glucofuranos-3'-yl)-azole derivatives is described.

The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process

A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.

REACTIONS OF HYDROXYL GROUPS WITH TOSYLCHLORIDE-DIMETHYLAMINOPYRIDINE SYSTEM. DIRECT SYNTHESIS OF CHLORIDES FROM HYDROXYCOMPOUNDS.

The reactions of various hydroxyl groups with tosylchloride-dimethylaminopyridine system were investigated and direct synthesis of allyl, alkyl and glycosyl chlorides are described.