26597-74-0

Basic information

• Product Name: 1,2:5,6-di-O-isopropylidene-β-L-talofuranose
• Synonyms: 1,2:5,6-di-O-isopropylidene-β-L-talofuranose
• CAS NO: 26597-74-0
• Molecular Weight: 260.287
• Mol File: 26597-74-0.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1,2:5,6-di-O-isopropylidene-β-L-talofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-di-O-isopropylidene-β-L-talofuranose(26597-74-0)
• EPA Substance Registry System: 1,2:5,6-di-O-isopropylidene-β-L-talofuranose(26597-74-0)

Safety Data

• Hazardous Substances Data: 26597-74-0(Hazardous Substances Data)

Usage

Chemical compound

A derivative of talofuranose, a rare sugar.

Synthesis

Derived from the reaction of talofuranose with acetone in the presence of an acid catalyst.

Functionality

Often used in organic synthesis as a protecting group for the hydroxyl groups of sugars.

Selectivity

Can be selectively removed under mild conditions without affecting other functional groups.

Application

Used as a building block in the synthesis of complex organic molecules, particularly in the field of carbohydrate chemistry.

Industrial relevance

Has potential applications in the pharmaceutical and agrochemical industries.

Material development

Utilized in the development of new materials.

Upstream product

• 67-64-1 acetone 
• 121701-18-6 1,2-O-isopropylidene-α-L-glucofuranose 
• 2280-44-6 D-Glucose 
• 77-76-9 2,2-dimethoxy-propane 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-β-D-altrofuranose 
• 41846-94-0 D-altrose 
• 29586-98-9 3-O-acetyl-1,2,5,6-di-isopropylidene-α-D-glucofuranose 
• 26623-16-5 1,2:5,6-di-O-isopropylidene-β-D-arabino-hexofuranos-3-ulose 
• 16713-80-7 Acetic acid (3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 50-99-7 D-glucose 
• 1990-29-0 D-altrose 
• 6027-42-5 (2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol 
• 921-60-8 L-glucose 

Downstream Products

• 131791-66-7 Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester 
• 131791-64-5 Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-2-ylmethyl ester 
• 19189-62-9 Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester 
• 134275-38-0 1,2:5,6-di-O-isopropylidene-3-O-benzyl-β-D-altrofuranose 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 83167-68-4 (3aS,5S,6S,6aS)-2,2-Dimethyl-5-(1-phenylphosphinoyl-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 134275-39-1 3-O-benzyl-1,2-O-isopropylidene-β-D-altrofuranose 
• 134275-48-2 (5R and 5S)-5,6-dideoxy-1,2-O-isopropylidene-5-<(R and S)-(methoxy)phenylphosphinyl>-β-D-arabino-hexofuranoses 
• 134275-46-0 (5R and 5S)-5,6-dideoxy-1,2-O-isopropylidene-5-<(R and S)-(methoxy)phenylphosphinyl>-3-O-benzyl-β-D-arabino-hexofuranoses 
• 37073-74-8 3-O-benzyl-1,2-O-isopropylidene-6-O-tosyl-β-D-arabino-hexofuranos-5-ulose 
• 134275-41-5 3-O-benzyl-1,2-O-isopropylidene-6-O-tosyl-β-D-altrofuranose 
• 134275-44-8 (5R and 5S)-5,6-anhydro-1,2-O-isopropylidene-5-<(R and S)-(methoxy)phenylphosphinyl>-3-O-benzyl-β-D-arabino-hexofuranoses 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Relevant articles and documents

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.

Synthesis of a MUC1-glycopeptide-BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen-Friedenreich antigen

A novel MUC1-glycopeptide-BSA conjugate vaccine with a specifically fluorinated Thomsen-Friedenreich antigen side chain at Thr6 was prepared. Preliminary immunological experiments reveal specific binding of the tumor-associated glycopeptide antigen analog by anti-MUC1-mouse antibodies.