302579-06-2

Basic information

• Product Name: 2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate
• Synonyms: 2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate
• CAS NO: 302579-06-2
• Molecular Weight: 272.279
• Mol File: 302579-06-2.mol

Chemical Properties

• CAS DataBase Reference: 2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate(302579-06-2)
• EPA Substance Registry System: 2,4-O-benzylidene-D-erythritol-1,3-cyclic-sulfate(302579-06-2)

Safety Data

• Hazardous Substances Data: 302579-06-2(Hazardous Substances Data)

Upstream product

• 117122-84-6 (2R,4S,5R)-2-phenyl-5-hydroxy-1,3-dioxane-4-methanol 
• 334024-21-4 2,4-O-benzylidene-D-erythritol-1,3-cyclic sulfite 

Downstream Products

• 791627-62-8 2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-[[N-(2R,3R)-2,4-O-benzylidene-2,4-dihydroxy-3-(sulfooxy)butyl]-(R)-episulfoniumylidene]xylitol inner salt 
• 877463-77-9 (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2R,4R,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate 
• 877463-75-7 (2R,3S)-1,3-O-benzylidene-1,3-dihydroxy-4-[(2S,4S,5R)-2-benzyloxymethyl-4,5-dihydroxypiperidinium-1-yl]butane-2-sulfate 
• 913619-28-0 1,3:4,6-di-O-benzylidene-2,5-dideoxy-1,5-[[(2R,3R)-2,4-O-benyzlidene-2,4-dihydroxy-3-(sulfooxy)butyl]sulfoniumylidene]-L-iditol inner salt 
• 913534-58-4 1,3:4,6-di-O-benzylidene-2,5-dideoxy-1,5-[[(2R,3R)-2,4-O-benzylidene-2,4-dihydroxy-3-(sulfooxy)butyl]iminonium]-L-iditol 

Relevant articles and documents

Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity

De-O-sulfonated analogs (10a, Y- = CH3OSO3 and 10b, Y- = Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y- = CH3OSO3) with l-thiosugar moiety (1,4-dideoxy-1,4-epithio-l-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent α-glycosidase inhibitor, salacinol (1a). Compounds 10a and 10b showed a potent inhibitory activity equal to that of 1a against both enzymes, although 12a was a weak inhibitor against sucrase and maltase. These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity.

A new class of glycosidase inhibitor: Synthesis of salacinol and its stereoisomerst

Salacinol (4) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The syntheses of salacinol (4), the enantiomer of salacinol (5), and a diastereomer (7) are described. The synthetic strategy relies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D- or L-arabinitol at C-1 of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate. The work serves to resolve the ambiguity about the exact structure of salacinol and establishes conclusively the structure of the natural product.

Synthesis of salacinol

Salacinol, a new type of α-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sul