78574-35-3

Basic information

• Product Name: b-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 4-methylbenzenesulfonate
• CAS NO: 78574-35-3
• Molecular Formula: C19H26O8S
• Molecular Weight: 414.477
• Mol File: 78574-35-3.mol

Chemical Properties

• CAS DataBase Reference: b-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 4-methylbenzenesulfonate(78574-35-3)
• EPA Substance Registry System: b-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 4-methylbenzenesulfonate(78574-35-3)

Safety Data

• Hazardous Substances Data: 78574-35-3(Hazardous Substances Data)

Upstream product

• 57-48-7 D-Fructose 
• 20880-92-6 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 85973-55-3 O¹-(toluene-4-sulfonyl)-D-fructose 
• 943241-16-5 2,3-O-isopropylidene-1-O-p-tolylsulfonyl-β-D-fructopyranose 
• 75414-43-6 1,5-D-anhydrofructose 
• 103536-55-6 methyl-[O¹-(toluene-4-sulfonyl)-α-D-fructofuranoside] 

Relevant articles and documents

Sterically Strained Br?nsted Pair Catalysis by Bulky Pyridinium Salts: Direct Stereoselective Synthesis of 2-Deoxy and 2,6-Dideoxy-β-thioglycosides from Glycals

A sterically strained ionic Br?nsted pair complex obtained from a sterically bulky base 2,4,6-tri-tert-butylpyridine and hydrochloric acid imbues unusual reactivity to the anionic chloride. The complete shielding of the cationic [N-H]+ by the bulky ortho-

Radiolabeling and in vitro evaluation of a new 5-fluorouracil derivative with cell culture studies

The clinical impact and accessibility of 99mTc tracers for cancer diagnosis would be greatly enhanced by the availability of a new, simple, and easy labeling process and radiopharmaceuticals. 5-Fluorouracil is an antitumor drug, which has played an important role for the treatment of breast carcinoma. In the present study, a new derivative of 5-Fluorouracil was synthesized as (1-[{1′-(1′′-deoxy-2′′,3′′:4′′,5′′-di-O-isopropylidene-β-D-fructopyranose-1′′-yl)-1′H-1′,2′, 3′-triazol-4′-yl}methyl]-5-fluorouracil) (E) and radiolabeled with 99mTc. It was analyzed by radio thin layer chromatography for quality control and stability. The radiolabeled complex was subjected to in vitro cell-binding studies to determine healthy and cancer cell affinity using HaCaT and MCF-7 cells, respectively. In addition, in vitro cytotoxicity studies of compound E were performed with HaCaT and MCF-5 cells. The radiochemical purity of the [99mTc]TcE was found to be higher than 90% at room temperature up to 6 hours. The radiolabeled complex showed higher specific binding to MCF-7 cells than HaCaT cells. IC50 values of E were found 31.5 ± 3.4 μM and 20.7 ± 2.77 μM for MCF-7 and HaCaT cells, respectively. The results demonstrated the potential of a new radiolabeled E with 99mTc has selective for breast cancer cells.

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.

3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

Carbohydrate biguanides as potential hypoglycemic agents

A series of monosaccharides containing a biguanide functionality was prepared and evaluated for hypoglycemic activity. Among the analogues prepared were those involving D-glucose substituted on the 6- or 1- position (19 and 24), D-galactose substituted on