25018-67-1

Basic information

• Product Name: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE
• Synonyms: 2,3:4,5-bis-O-(1-methylethylidene)-;1,2:4,5-Di-O-isopropylidene-beta-D-fructopyrase;1,2:4,5-Di-O-isopropylidene-β-D-fructopyranose;(3aR,4'S,7S,7aS)-2,2,2',2'-tetraMethyltetrahydrospiro[[1,3]dioxolo[4,5-c]pyran-6,4'-[1,3]dioxolan]-7-ol;1,2:4,5-bis-O-(1-Methylethylidene)-β-D-Fructopyranose;1,2,4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE;1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE;B-D-FRUCTOPYRANOSE
• CAS NO: 25018-67-1
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• Product Categories: Sugars, Carbohydrates & Glucosides;chiral
• Mol File: 25018-67-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 116-117 °C
• Boiling Point: 379.03 °C at 760 mmHg
• Flash Point: 183.031 °C
• Appearance: /
• Density: 1.287 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.88±0.60(Predicted)
• CAS DataBase Reference: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE(25018-67-1)
• EPA Substance Registry System: 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSE(25018-67-1)

Safety Data

• Hazardous Substances Data: 25018-67-1(Hazardous Substances Data)

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 articles and documents

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.

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.