187590-77-8

Basic information

• Product Name: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol
• Synonyms: 1,4-Dideoxy-1,4-epithio-2,3,5-tris-O-(phenylmethyl)-D-arabinitol;(2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene;1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol
• CAS NO: 187590-77-8
• Molecular Formula: C₂₆H₂₈O₃S
• Molecular Weight: 420.56372
• Mol File: 187590-77-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol(187590-77-8)
• EPA Substance Registry System: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol(187590-77-8)

Safety Data

• Hazardous Substances Data: 187590-77-8(Hazardous Substances Data)

Usage

Description

2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol is a synthetic organic compound that serves as an intermediate in the synthesis of Salacinol (S085200), a natural α-glucosidase inhibitor derived from the herb Salacia reticulata. 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol is characterized by its unique structure, featuring three benzyl groups attached to the 2, 3, and 5 positions, and a 1,4-dideoxy-1,4-epithio bridge, which contributes to its potential applications in various fields.

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 this compound 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

• 942610-80-2 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-{(S)-[(2S,3S)-2,4-O-isopropylidene-3-(sulfooxy)butyl]episulfonioylidene}-D-arabinitol 
• 15023-77-5 1-(6-amino-purin-9-yl)-β-D-4-thio-1-deoxy-arabinofuranose 
• 169736-20-3 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-D-arabinofuranose 
• 191794-46-4 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 191794-45-3 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-ethyl-1H-pyrimidine-2,4-dione 
• 191794-47-5 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-iodo-1H-pyrimidine-2,4-dione 
• 191794-48-6 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-((E)-2-chloro-vinyl)-1H-pyrimidine-2,4-dione 
• 191794-49-7 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-((E)-2-bromo-vinyl)-1H-pyrimidine-2,4-dione 
• 191794-52-2 7-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-7H-purin-6-ylamine 
• 191794-50-0 9-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-9H-purin-6-ylamine 
• 191794-55-5 9-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-9H-purine-2,6-diamine 
• 6741-71-5 5-methyl-1-(4-thio-α-D-arabinofuranosyl)uracil 
• 4303-00-8 (2S,3S,4S,5R)-2-(6-Amino-purin-9-yl)-5-hydroxymethyl-tetrahydro-thiophene-3,4-diol 
• 26527-36-6 5-methyl-1-(β-D-4-thio-arabinofuranosyl)-1H-pyrimidine-2,4-dione 

Relevant articles and documents

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.

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

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.