187590-77-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol is used as a key intermediate in the synthesis of Salacinol, an antidiabetic agent. Salacinol has been found to inhibit the activity of α-glucosidase, an enzyme responsible for breaking down carbohydrates into glucose, thus helping to regulate blood sugar levels in diabetic patients.
Used in Drug Development:
As a precursor in the synthesis of Salacinol, 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol plays a crucial role in the development of new antidiabetic drugs. Researchers can use 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol to explore and optimize the synthesis process, potentially leading to the discovery of more effective and safer treatments for diabetes.
Used in Chemical Research:
The unique structure of 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol also makes it a valuable compound for chemical research. Scientists can study its properties and reactivity to gain insights into the behavior of similar compounds and develop new synthetic strategies or applications in various fields, such as materials science or pharmaceuticals.

Upstream product

• 100-39-0 benzyl bromide 
• 160882-26-8 (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol 
• 135910-18-8 (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane 
• 160882-25-7 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 
• 100-44-7 benzyl chloride 

Downstream Products

• 187590-79-0 (2R,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-tetrahydro-thiophene 1-oxide 
• 1159101-26-4 BF₄^(1-)*C₄₄H₄₉O₆S⁽¹⁺⁾ 
• 1159101-28-6 BF₄^(1-)*C₄₄H₄₉O₆S⁽¹⁺⁾ 
• 1220095-40-8 C₇H₇O₃S^(1-)*C₃₃H₄₁O₈S⁽¹⁺⁾ 
• 1220095-47-5 C₇H₇O₃S^(1-)*C₃₉H₄₅O₈S⁽¹⁺⁾ 
• 1220095-44-2 C₇H₇O₃S^(1-)*C₃₉H₄₅O₈S⁽¹⁺⁾ 
• 1254190-34-5 CF₃O₃S^(1-)*C₅₄H₅₉O₈S⁽¹⁺⁾ 

Relevant academic research and scientific papers

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.

Compound useful for producing [...] and their production, production of [...], diol protecting group of deprotection method and method, as well as diol protecting groups (by machine translation)

[A] producing a novel compound useful [...] and their production, production of [...], diol protecting group of deprotection method and method, as well as diol protecting group of agents. [Solution]General formula (7a)(In the formula, R4Ba The, p - torr oil group. ) Is a compound represented by, [...] useful for producing compounds. [Drawing] no (by machine translation)

COMPOUNDS USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE SAME, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP

PROBLEM TO BE SOLVED: To provide novel compounds useful for manufacturing salacinol, a method for manufacturing the compounds, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. SOLUTION: A compound represented by formula (7a) is a compound useful for manufacturing salacinol. (In the formula, R4ba is a p-toluoyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

COMPOUND USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE COMPOUND, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP

An object of the present invention is to provide a novel compound useful for manufacturing salacinol, a method for manufacturing the compound, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. A compound represented by Formula (1) is a compound useful for manufacturing salacinol. (In the formula, each of R1a and R1b is a hydrogen atom or a hydroxy protective group; R2 is a hydroxy group or the like; and R3 is a hydroxy group or the like.)

GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME

The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

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.

Glycosidase inhibitors and methods of synthesizing same

A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes c

Glycosidase inhibitors and methods of synthesizing same

A method for synthesizing Salacinol, its stereoisomers, and non-naturally occurring selenium and nitrogen analogues thereof having the general formula (I): The compounds are potentially useful as glycosidase inhibitors. The synthetic schemes comprise reac

A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities

4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hy