1240304-31-7

Basic information

• Product Name: (1S)-2,3,4,6-tetra-O-acetyl-1-[2-(acetyloxy)-5-[(4-bromo-2-methylphenyl)methyl]-4-(propan-2-yl)phenyl]-1,5-anhydro-D-glucitol
• Synonyms: (1S)-2,3,4,6-tetra-O-acetyl-1-[2-(acetyloxy)-5-[(4-bromo-2-methylphenyl)methyl]-4-(propan-2-yl)phenyl]-1,5-anhydro-D-glucitol
• CAS NO: 1240304-31-7
• Molecular Weight: 691.57
• Mol File: 1240304-31-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S)-2,3,4,6-tetra-O-acetyl-1-[2-(acetyloxy)-5-[(4-bromo-2-methylphenyl)methyl]-4-(propan-2-yl)phenyl]-1,5-anhydro-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-2,3,4,6-tetra-O-acetyl-1-[2-(acetyloxy)-5-[(4-bromo-2-methylphenyl)methyl]-4-(propan-2-yl)phenyl]-1,5-anhydro-D-glucitol(1240304-31-7)
• EPA Substance Registry System: (1S)-2,3,4,6-tetra-O-acetyl-1-[2-(acetyloxy)-5-[(4-bromo-2-methylphenyl)methyl]-4-(propan-2-yl)phenyl]-1,5-anhydro-D-glucitol(1240304-31-7)

Safety Data

• Hazardous Substances Data: 1240304-31-7(Hazardous Substances Data)

Upstream product

• 1359948-58-5 C₃₆H₄₃BrO₁₄ 
• 108-24-7 acetic anhydride 
• 1240304-51-1 C₃₃H₃₉BrO₁₂ 
• 1017608-23-9 2-iodo-5-(propan-2-yl)phenol 
• 618-45-1 3-isopropylhydroxybenzene 
• 1240304-54-4 1,5-dibromo-2-(methoxymethoxy)-4-(propan-2-yl)benzene 
• 1240304-35-1 2-(benzyloxy)-1-iodo-4-(propan-2-yl)benzene 
• 1359948-57-4 C₂₄H₃₁BrO₈ 
• 1359948-56-3 C₄₀H₇₃BrO₉Si₅ 
• 1240304-42-0 (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[2-hydroxy-4-(propan-2-yl)phenyl]-D-glucitol 
• 1240304-44-2 (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[5-bromo-2-hydroxy-4-(propan-2-yl)phenyl]-D-glucitol 
• 1240304-37-3 (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[2-(benzyloxy)-4-(propan-2-yl)phenyl]-D-glucitol 
• 1240304-46-4 (1S)-1,5-anhydro-1-{5-bromo-4-(propan-2-yl)-2-[(trimethylsilyl)oxy]phenyl}-2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucitol 
• 24078-12-4 4-bromo-2-methylbenzaldehyde 

Downstream Products

• 1369430-79-4 C₃₉H₄₈O₁₃ 
• 1369430-76-1 C₄₃H₅₅NO₁₄ 
• 1369430-81-8 C₃₇H₅₅N₃O₈ 
• 1369430-92-1 C₃₇H₅₅N₃O₈ 
• 1369430-91-0 C₄₇H₆₅N₃O₁₃ 
• 1369430-80-7 C₄₇H₆₅N₃O₁₃ 
• 1369430-89-6 C₅₀H₆₉N₃O₁₃ 
• 1369430-93-2 C₅₂H₇₃N₃O₁₅ 

Relevant articles and documents

Synthesis and structure-activity relationship of C-phenyl D-glucitol (TP0454614) derivatives as selective sodium-dependent glucose cotransporter 1 (SGLT1) inhibitors

Sodium-glucose cotransporter 1 (SGLT1) is the primary transporter for glucose absorption from the gastrointestinal tract. While C-phenyl D-glucitol derivative SGL5213 has been reported to be a potent intestinal SGLT1 inhibitor for use in the treatment of type 2 diabetes, no SGLT1 selectivity was found in vitro (IC50 29 nM for hSGLT1 and 20 nM for hSGLT2). In this study we found a new method of synthesizing key intermediates 12 by a one-pot three-component condensation reaction and discovered C-phenyl D-glucitol 41j (TP0454614), which has >40-fold SGLT1 selectivity in vitro (IC50 26 nM for hSGLT1 and 1101 nM for hSGLT2). The results of our study have provided new insights into the structure-activity relationships (SARs) of the SGLT1 selectivity of C-glucitol derivatives.

4 -ISOPROPYLPHENYL GLUCITOL COMPOUNDS AS SGLTL INHIBITORS

The present invention provides 4-isopropylphenyl glucitol compounds which have no tendency to accumulate in the body and which inhibit SGLT1 activity to suppress postprandial hyperglycemia (or impaired glucose tolerance) through suppression of glucose absorption in the small intestine, whereby the compounds, for example, can suppress the onset of diabetes and metabolic syndrome or can treat these diseases. A 4-isopropylphenyl glucitol compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof: [Chem. 1] wherein R1 represents a hydrogen atom, etc., R2 represents a methyl group, etc., R3 represents a C1-4 alkyl group substituted with an amino group(s), etc., and R4 represents a hydrogen atom, etc.