25018-67-1

Usage

Uses

1,2:4,5-Di-O-Isopropylidine-beta-D-fructopyranose is used as a reagent in the synthesis of various biologically active compounds due to its unique structural features and reactivity.
Used in Pharmaceutical Industry:
1,2:4,5-Di-O-Isopropylidine-beta-D-fructopyranose is used as a key intermediate for the synthesis of antibacterial and antifungal monosaccharide esters. These esters have potential applications in the development of new drugs to combat bacterial and fungal infections, which are increasingly becoming resistant to existing treatments.
Used in the Synthesis of Antihyperlipidemic Compounds:
1,2:4,5-Di-O-Isopropylidine-beta-D-fructopyranose is also used in the synthesis of novel compounds with antihyperlipidemic properties, specifically involving glycosyl fructose derivatives. These compounds may have potential applications in the treatment of hyperlipidemia, a condition characterized by high levels of lipids in the blood, which can increase the risk of cardiovascular diseases.

Upstream product

• 57-48-7 D-Fructose 
• 67-64-1 acetone 
• 57-50-1 Sucrose 
• 512-69-6 D-raffinose 
• 7664-93-9 sulfuric acid 
• 7660-25-5 D-fructose 
• 77-76-9 2,2-dimethoxy-propane 
• 57-48-7 L-fructose 
• 57-48-7 fructose 
• 20880-92-6 2,3:4,5-di-O-isopropylidene-β-L-fructopyranose 

Downstream Products

• 41342-39-6 O¹,O²;O⁴,O⁵-diisopropylidene-O³-(toluene-4-sulfonyl)-β-D-fructopyranose 
• 898285-45-5 O³-diphenoxyphosphoryl-O¹,O²;O⁴,O⁵-diisopropylidene-β-D-fructopyranose 
• 126247-74-3 D-arabino-1,4,5,6-Tetrahydroxy-3-phosphonooxy-hexan-2-on 
• 85458-76-0 3-O-Benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose 
• 13403-14-0 methyl D-fructofuranoside 
• 76573-34-7 (-)-3-deoxy-1,2:4,5-di-O-isopropylidene-β-D-fructofuranos-3-yl benzoate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 89387-58-6 1,2:4,5-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-fructopyranose 
• 69351-19-5 Shi's ketone 
• 20880-92-6 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 341489-97-2 1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl benzyloxyacetate 

Relevant academic research and scientific papers

A mild acetolysis procedure for the regioselective removal of isopropylidene in di-O-isopropylidene-protected pyranoside systems

A mild acetolysis method for the regioselective removal of isopropylidene group from di-O-isopropylidene-protected hexopyranosides is reported. O-Isopropylidene-protected intermediates play an important role in carbohydrate chemistry, as they are often found in commercially available furanosyl and pyranosyl materials, and some of them contain more than one O-isopropylidene groups. Methods that permit regioselective removal of O-isopropylidene groups are extremely valuable, as the number of steps in the total synthesis of complex oligosaccharides could be significantly decreased. Here we report that trifluoroacetic acid (TFA)/acetic anhydride (Ac2O) can be used to regioselectively convert one of the two O-isopropylidene groups to vicinal di-O-acetates in the di-O-isopropylidene-protected galacto- and fructo-pyranosyl systems, and the reagent is compatible with some common functionalities such as sulfonate esters, bromide, azide etc.

d-Fructose Modification Enhanced Internalization of Mixed Micelles in Breast Cancer Cells via GLUT5 Transporters

d-Fructose modified poly(ε-caprolactone)-polyethylene glycol (PCL-PEG-Fru) diblock amphiphile is synthesized via Cu(I)-catalyzed click chemistry, which self-assembles with D-α-tocopheryl polyethylene glycol 1000 succinate (TPGS) into PCL-PEG-Fru/TPGS mixed micelles (PPF MM). It has been proven that glucose transporter (GLUT)5 is overexpressed in MCF-7 cells other than L929 cells. In this study, PPF MM exhibit a significantly higher uptake efficiency than fructose-free PCL-PEG-N3/TPGS mixed micelles in both 2D MCF-7 cells and 3D tumor spheroids. Also, the presence of free d-fructose competitively inhibits the internalization of PPF MM in MCF-7 cells other than L929 cells. PPF MM show selective tumor accumulation in MCF-7 breast tumor bearing mice xenografts. Taken together, PPF MM represent a promising nanoscale carrier system to achieve GLUT5-mediated cell specific delivery in cancer therapy. (Figure presented.).

Concise synthesis of chiral N -Benzyl-α,α-Diarylprolinols through shi asymmetric epoxidation

A concise and practical synthesis of chiral N-benzyl-α,α- diaryl-2-prolinols was developed through Shi asymmetric epoxidation, followed by double nucleophilic substitution of bromo-containing olefins. A series of enantioenriched N-benzyl-α,α-diaryl-2-prolinols were obtained with excellent enantioselectivities (96% ee) in moderate to good yields (40-76% yield). For the first time, enantiopure N-benzyl-α,α-diphenyl-2- prolinol was obtained from bromo-containing olefin using this methodology. Georg Thieme Verlag Stuttgart, New York.

An epoxidation approach to a chiral lactone: Application of the Shi epoxidation

The large-scale epoxidation of the alkene 7 with the organo-catalyst, Epoxone (10), and Oxone as the oxidant is described. This is the first large-scale application of the Shi epoxidation methodology. The large-scale preparation of the catalyst 10 is also described. The potassium salt of the unsaturated acid precursor 7 was prepared by a Suzuki coupling from 3-fluorobenzyl chloride and the vinylborane 8 derived from 4-pentynoic acid.

Acetalation studies. Part IX. Reaction of sucrose and some related sugars with acetone in the presence of iodine; a novel cleavage-isopropylidenation method

An efficient cleavage-isopropylidenation reaction of sucrose, catalyzed by iodine, is described.Related D-fructofuranosyl-containing oligosaccharides and their individual monosaccharide units were treated in a similar manner to yield isopropylidenated monosaccharide derivatives.The reaction conditions are particularly mild and selective.Some mechanistic aspects of the procedure are also discussed.

Synthesis of Polymerizable Hexose Derivatives

Polymerizable esters of methacrylic and acrylic acid with di-O-isopropylidenehexoses as alcohol components have been synthesized.

GAS CHROMATOGRAPHY-MASS SPECTROMETRY OF HEXULOSES AND PENTULOSES AS THEIR O-ISOPROPYLIDENE DERIVATIVES: ANALYSIS OF PRODUCT MIXTURES FROM TRIOSE ALDOL-CONDENSATIONS

Identification and quantitation of hexuloses and pentuloses in mixtures has been achived by gas chromatography-mass spectrometry of their O-isopropylidene derivatives.The method has been applied to product mixtures from triose aldol-condensations.The use of strongly basic anion-exchange resins as catalysts in the aldol condensation gives considerably higher proportions of fructose than when alkali or alkaline-earth hydroxides are applied.