4478-43-7

Usage

Uses

Used in Pharmaceutical Industry:
1,2:3,4-Di-O-isopropylidene-6-O-p-tolylsulfonyl-alpha-D-galactose is used as a specialized chemical intermediate for the synthesis of complex organic compounds in the pharmaceutical industry. Its unique structure and reactivity make it a valuable component in the development of novel pharmaceutical agents.
Used in Chemical Manufacturing:
In the chemical manufacturing industry, 1,2:3,4-Di-O-isopropylidene-6-O-p-tolylsulfonyl-alpha-D-galactose is utilized as a key reactant in the production of various organic compounds. Its sulfonate group and O-glycosidic bond contribute to the formation of new chemical entities with potential applications in various fields.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 59-23-4 D-Galactose 
• 3646-73-9 α-D-galactopyranose 
• 67-64-1 acetone 
• 10257-28-0 D-Galactose 
• 6748-86-3 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 
• 536-57-2 p-toluene sulfinic acid 
• 34698-19-6 methyl 6-O-tosyl-α-D-galactopyranoside 
• 79378-77-1 1,2:3,4-Di-O-isopropyliden-6-O-(p-tolylsulfinyl)-α-D-galactopyranose 

Downstream Products

• 16714-06-0 6-S-acetyl-6-deoxy-1,2:3,4-di-O-isopropylidene-6-thio-α-D-galactopyranose 
• 106248-66-2 1,2,3,4-tetra-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-galactopyranose  
• 106192-43-2 2,3,4-Tri-O-acetyl-6-O-(p-tolylsulfonyl)-β-D-galactopyranosylazid 
• 129171-96-6 methyl 3,4-O-benzylidene-6-deoxy-D-galactopyranoside 
• 119824-72-5 C₂₁H₂₁⁽²⁾HO₆ 
• 3615-37-0 D-Fucose 
• 100574-17-2 (-)-6-benzoylamino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 949466-63-1 6-deoxy-1,2:3,4-di-O-isopropylidene-6-phenylselenyl-α-D-galactopyranose 
• 1607008-37-6 C₅₈H₈₀N₂O₁₀ 

Relevant academic research and scientific papers

Synthesis of novel amidoxime-linked pseudodisaccharides

Disaccharide analogues containing amidoxime interglycosidic linkages have been synthesised by nucleophilic addition of aminomethylene pyranoses to pyranosyl nitrile oxides, generated by dehydrochlorination of the corresponding hydroximoyl chlorides. The s

Synthesis and biological evaluation of benzo[f]indole-4,9-diones n-linked to carbohydrate chains as new type of antitumor agents

In this work, we report the synthesis of three series of carbohydrate-based benzo[f]indole-4,9-diones and amino-1,4-naphthoquinone derivatives and evaluated their cytotoxic activity against eight human cancer cell lines. Several compounds showed a promising cytotoxic activity toward the tumor cell lines (half maximal inhibitory concentration (IC50) 10.0 μM). The importance of the substitution pattern of the quinone derivatives on the antitumor activity was also discussed. 3-Carboethoxy-2-methyl-benzo[f]indole-4,9-dione derivatives were more cytotoxic than their parent compounds and amino-1,4-naphthoquinones. Unlike clinically useful anticancer agent doxorubicin, the majority of synthesized compounds did not exhibit any lytic effects against erythrocytes or normal human leukocytes.

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%.

Synthesis and antimicrobial evaluation of amino sugar-based naphthoquinones and isoquinoline-5,8-diones and their halogenated compounds

Antibiotic resistance has emerged as a serious global public health problem and lately very few antibiotics have been discovered and introduced into clinical practice. Therefore, there is an urgent need for the development of antibacterial compounds with new mechanism of action, especially those capable of evading known resistance mechanisms. In this work two series of glycoconjugate and non-glycoconjugate amino compounds derived from of isoquinoline-5,8-dione and 1,4-naphthoquinone and their halogenated derivatives were synthesized and evaluated for antimicrobial activity against Gram-positive (Enterococcus faecalis ATCC 29212, Staphylococcus aureus ATCC 25923, S. epidermidis ATCC 12228, S. simulans ATCC 27851) and Gram-negative bacteria (E. coli ATCC 25922, Proteus mirabilis ATCC 15290, K. pneumoniae ATCC 4352 and P. aeruginosa ATCC 27853) strains of clinical importance. This study revealed that glycoconjugate compounds derived from halogeno-substituted naphthoquinones were more active against Gram-negative strains, which cause infections whose treatment is even more difficult, according to the literature. These molecules were also more active than isoquinoline-5,8-dione analogues with minimum inhibitory concentration (MIC = 4–32 μg/mL) within Clinical and Laboratory Standard Institute MIC values (CLSI 0.08–256 μg/mL). Interestingly the minimal bactericidal concentration (MBC) values of the most active compounds were equal to MIC classifying them as bactericidal agents against Gram-negative bacteria. Sixteen compounds among eighteen carbohydrate-based naphthoquinones tested showed no hemolytic effects on health human erythrocytes whereas more susceptibility to hemolytic cleavage was observed when using non-glycoconjugate amino compounds. In silico Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) evaluation also pointed out that these compounds are potential for oral administration with low side effects. In general, this study indicated that these compounds should be exploited in the search for a leading substance in a project aimed at obtaining new antimicrobials more effective against Gram-negative bacteria.

Design, synthesis, cholinesterase inhibition and molecular modelling study of novel tacrine hybrids with carbohydrate derivatives

A series of hybrids containing tacrine linked to carbohydrate-based moieties, such as D-xylose, D-ribose, and D-galactose derivatives, were synthesized by the nucleophilic substitution between 9-aminoalkylamino-1,2,3,4-tetrahydroacridines and the corresponding sugar-based tosylates. All compounds were found to be potent inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) in the nanomolar IC50 scale. Most of the D-xylose derivatives (6a-e) were selective for AChE and the compound 6e (IC50 = 2.2 nM for AChE and 4.93 nM for BuChE) was the most active compound for both enzymes. The D-galactose derivative 8a was the most selective for AChE exhibiting an IC50 ratio of 7.6 for AChE over BuChE. Only two compounds showed a preference for BuChE, namely 7a (D-ribose derivative) and 6b (D-xylose derivative). Molecular docking studies indicated that the inhibitors are capable of interacting with the entire binding cavity and the main contribution of the linker is to enable the most favorable positioning of the two moieties with CAS, PAS, and hydrophobic pocket to provide optimal interactions with the binding cavity. This finding is reinforced by the fact that there is no linear correlation between the linker size and the observed binding affinities. The majority of the new hybrids synthesized in this work do not violate the Lipinski's rule-of-five according to FAF-Drugs4, and do not demonstrated predicted hepatotoxicity according ProTox-II.

3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides

A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors.

Introducing Glycolinkers for the Functionalization of Cytotoxic Drugs and Applications in Antibody–Drug Conjugation Chemistry

Antibody–drug conjugates (ADCs) are promising alternatives to naked antibodies for selective drug-delivery applications and treatment of diseases such as cancer. Construction of ADCs relies upon site-selective, efficient and mild conjugation technologies.

Synthesis of a new class of naphthoquinone glycoconjugates and evaluation of their potential as antitumoral agents

A novel series of carbohydrate-based naphthoquinones was synthesized and evaluated for cytotoxicity against different cancer cell lines. The compounds derived from 5-hydroxy-1,4-naphthoquinone (juglone) showed better cytotoxicity profiles against HCT-116, A-549 and MDA-MB 435 human cancer cells than the parent compound. The results suggest that the hydroxyl group on the aromatic ring increased the pro-oxidant activity of these new naphthoquinone derivatives. Furthermore, two derivatives were found to be more active against melanoma cells (MDA-MB435) than the clinically useful anticancer agent doxorubicin, and none of the compounds caused mouse erythrocyte lysis.

Thermoresponsive copolymers with pendant d-galactosyl 1,2,3-triazole groups: Synthesis, characterization and thermal behavior

A galactose containing glycomonomer has been synthesized by copper catalyzed azide-alkyne cyclo-addition reaction (CuAAC) of 6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose with propargyl acrylate. This monomer was subjected to homopolymerization and copolymerization with N-isopropylacrylamide (NIPAm) at different compositions by free radical polymerization using 2,2′-azobis-isobutyronitrile (AIBN) as an initiator. The composition of the copolymer was determined by 1H-NMR spectroscopy. Upon acid hydrolysis of acetonide protected polymers, water-soluble deprotected polymers were obtained. The polymers were characterized and confirmed by NMR, IR, GPC and thermal analytical techniques. The protected and deprotected copolymers showed a sharp cloud-point temperature and a linear correlation was obtained between the lower critical solution temperatures (LCST) and the concentration of glycomonomer in the copolymers. This allows tuning the thermal response by simply altering the copolymer composition. Water contact angle experiments showed the changes in the hydrophilicity of copolymers with compositions that supported the LCST results. The glass transition temperature of protected copolymers followed a regular monotonic decreasing trend with increasing glycomonomer content, whereas Tg of deprotected copolymers increased due to H-bond interaction. The attempts to develop thermoresponsive polymers having LCSTs at physiological temperature were successful.