16714-07-1

Usage

Uses

Used in Organic Synthesis:
1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose is used as a protecting group for the hydroxyl groups of sugars in organic synthesis. This allows for selective reactions to occur without affecting the rest of the molecule, facilitating the synthesis of more complex carbohydrate structures.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose is used as a key intermediate in the synthesis of new pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of biologically active compounds with potential therapeutic applications.
Used in the Preparation of Glycoside Derivatives:
1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose is utilized in the preparation of various glycoside derivatives, which are important in the synthesis of complex carbohydrates and other biologically relevant molecules. Its presence in these derivatives contributes to the structural diversity and functional properties of the resulting compounds.
Overall, 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose plays a crucial role in the advancement of organic synthesis, pharmaceutical development, and the creation of new materials and biologically active compounds. Its unique properties and applications make it an essential component in the field of chemistry and related industries.

Upstream product

• 4026-28-2 1,2:3,4-di-O-isopropylidene-6-iodo-D-galactopyranose 
• 3646-73-9 α-D-galactopyranose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 4478-43-7 (1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose 
• 71001-09-7 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose 
• 16714-06-0 6-S-acetyl-6-deoxy-1,2:3,4-di-O-isopropylidene-6-thio-α-D-galactopyranose 
• 10257-28-0 D-Galactose 

Downstream Products

• 1032633-96-7 1,2:3,4-di-O-isopropylidene-6-S-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-6-thio-α-D-galactopyranose 
• 1153940-53-4 1,2:3,4-di-O-isopropylidene-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-α-D-galactopyranose 
• 1201897-32-6 1,2;3,4-di-O-isopropylidene-6-thio-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-glucopyranosyl)-α-D-galactopyranoside 
• 1450629-16-9 C₄₆H₇₆O₉SSi₃ 
• 1450629-17-0 C₃₇H₅₂O₉SSi 
• 1333122-82-9 bis(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)-6,6′-disulfide 

Relevant academic research and scientific papers

Action of acid on 6-thio-hexose derivatives. Synthesis of 1,6-epithio-hexofuranoses

Reaction of 5,6-anhydro-1,2-O-isopropylidene-3-O-methanesulfonyl-β-L-idofuranose with thioacetic acid in pyridine gave 6-S-acetyl-1,2-O-isopropylidene-3-O-methanesulfonyl-6-thio-β-L-idofuranose, which was deacetylated and the resultant thiol was converted

Synthesis and membranoprotective properties of new disulfides with monoterpene and carbohydrate fragments

A cooxidation of carbohydrate and terpene thiols gives mixtures of disulfides containing 51 - 90% of the unsymmetric product. Membranoprotective and antioxidant properties of obtained unsymmetric and symmetric disulfides were evaluated based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes, as well as the accumulation of secondary products of the peroxy oxidation of lipids and the oxidation of hemoglobin.

Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates

Novel gold(I) and gold(III) complexes containing derivatives of d-galactose, d-ribose and d-glucono-1,5-lactone as ligands were synthesized and characterized by IR, 1H, and 13C NMR, high resolution mass spectra and cyclic voltammetry. The compounds were evaluated in vitro for their cytotoxicity against three types of tumor cells: cervical carcinoma (HeLa) breast adenocarcinoma (MCF-7) and glioblastoma (MO59J) and one non-tumor cell line: human lung fibroblasts (GM07492A). Their antitubercular activity was evaluated as well expressed as the minimum inhibitory concentration (MIC90) in μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (1) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (8) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity. The study of the cytotoxic activity revealed effective antitumor activities for the gold(I) complexes, being more active than cisplatin in all the tested tumor cell lines. Gold(I) compounds (1), (2), (3), (4) and (6) exhibited relevant antitubercular activity even when compared with first line drugs such as rifampicin.

Umpolung reactivity in the stereoselective synthesis of S-linked 2-deoxyglycosides

Take control! An unprecedented sulfenylation of stereochemically defined 2-deoxyglycosyl lithium species with asymmetric sugar-derived disulfide acceptors enabled the stereoselective synthesis of both α- and β-S-linked 2-deoxyoligosaccharides. Reductive lithiation of 2-deoxyglycosyl phenylsulfides at -78°C provides predominantly axial glycosyl lithium species, which upon warming isomerize to predominantly equatorial lithium species (see scheme). Copyright

A novel tin-free procedure for alkyl radical reactions

Desulfuration as a source of alkyl radicals: The addition of alkylsulfanyl radicals to isocyanides gives the corresponding alkyl radicals. This methodology can replace the usual tin-mediated radical procedures and allows for the generation of tertiary, secondary, and even nonstabilized primary radicals that can be used efficiently in reductive defunctionalizations and intermolecular additions to electron-rich olefins (see scheme).

Synthesis of some 6-S-heterocyclic derivatives of 1,2:3,4-Di-O-isopropylidene-α-D-galactopyranose

We applied nucleophilic substitution to 6-O-tosyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose using sulphur nucleophiles and obtained 6-S-derivatives of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. We present the physical and spectroscopic characterization of these heterocyclic compounds as well as other related compounds obtained by substitution, using other substrates. The conformational studies of all products are presented and discussed.