79943-22-9

Basic information

• Product Name: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE
• Synonyms: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE;(3aS,5R,6R,6aS)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS NO: 79943-22-9
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• Mol File: 79943-22-9.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE(79943-22-9)
• EPA Substance Registry System: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE(79943-22-9)

Safety Data

• Hazardous Substances Data: 79943-22-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE is utilized as a protecting group to temporarily block the reactivity of certain functional groups in sugar molecules during organic synthesis. This selective protection allows chemists to carry out reactions on specific sites of the molecule without affecting other areas, ensuring precise control over the synthesis process.
Used in Pharmaceutical Industry:
As a precursor, 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE is employed in the synthesis of various pharmaceutical compounds. Its unique chemical structure and reactivity make it a valuable component in the development of new drugs and therapeutic agents, contributing to advancements in medicine and healthcare.
Used in Sugar Derivative Synthesis:
1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-L-GLUCOFURANOSE also serves as a starting material for the production of diverse sugar derivatives. These derivatives have a wide range of applications, from biological research to the development of novel materials and compounds with specific properties.

Upstream product

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

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 
• 714967-70-1 3-O-acetyl-1,2-O-isopropylidene-6-O-trityl-α-L-glucofuranose 
• 90941-98-3 (S)-2-Benzenesulfinyl-3-[(4S,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol 
• 90941-85-8 (S)-2-Benzenesulfinyl-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethanol 
• 90941-83-6 (R)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol 
• 90941-83-6 (S)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-[(4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-1-ol 
• 4118-60-9 O¹,O²-isopropyliden-5,6-anhydro-α-L-glucofuranose 
• 121613-69-2 O¹,O²-isopropylidene-O⁶-(toluene-4-sulfonyl)-α-L-glucofuranose 
• 1338054-29-7 N-benzyl-1,2-O-isopropylidene-3,5-dideoxy-3,5-imino-α-L-xylofuranose 
• 1338054-34-4 N-(p-methoxybenzyl)-1,2-O-isopropylidene-3,5-dideoxy-3,5-imino-α-L-xylofuranose 
• 1338054-36-6 N-benzyl-1,3-dideoxy-1,3-imino-D-xylitol 
• 1338054-41-3 N-(p-methoxybenzyl)-1,3-dideoxy-1,3-imino-D-xylitol 

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.