16714-07-1

Basic information

• Product Name: 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose
• Synonyms: 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose;1,2:3,4-Di-O-isopropyliden- 6-deoxy-6-thio-alpha-D-galactopyranose;1,2:3,4-Di-O-isopropylidene-6-thio-α-D-galactopyranose;1,2:3,4-di-O-isopropylidene-6-deoxy-6-thio-α-D-galactopyranose;((3AR,5S,5AR,8AS,8BR)-2,2,7,7-TETRAMETHYLTETRAHYDRO-3AH-BIS([1,3]DIOXOLO)[4,5-B:4,5-D]PYRAN-5-YL)METHANETHIOL;3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose
• CAS NO: 16714-07-1
• Molecular Formula: C₁₂H₂₀O₅S
• Molecular Weight: 276.3492
• Product Categories: Carbohydrates
• Mol File: 16714-07-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 347.4±37.0 °C(Predicted)
• Appearance: /
• Density: 1.141±0.06 g/cm3(Predicted)
• PKA: 9.31±0.10(Predicted)
• CAS DataBase Reference: 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose(16714-07-1)
• EPA Substance Registry System: 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose(16714-07-1)

Safety Data

• Hazardous Substances Data: 16714-07-1(Hazardous Substances Data)

Usage

General Description

1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose is a chemical compound with a complex molecular structure. It is a derivative of a-D-galactopyranose with thiol and isopropylidene groups attached to specific carbon atoms. 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose is often used in organic synthesis as a protecting group for the hydroxyl groups of sugars, allowing for selective reactions to occur without affecting the rest of the molecule. It is also commonly used in the preparation of various glycoside derivatives and as a building block in the synthesis of more complex carbohydrates. Overall, 1,2:3,4-Di-O-isopropylidene-6-thio-a-D-galactopyranose plays a crucial role in the development of new pharmaceuticals, materials, and other biologically active compounds.

Upstream product

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

Downstream Products

• 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 
• 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 

Relevant articles and documents

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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