131757-92-1

Basic information

• Product Name: 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone
• Synonyms: 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone;(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one
• CAS NO: 131757-92-1
• Molecular Weight: 554.707
• Mol File: 131757-92-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone(131757-92-1)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone(131757-92-1)

Safety Data

• Hazardous Substances Data: 131757-92-1(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone is a chemical compound with the molecular formula C34H32O5S. It is a derivative of D-glucono-1,5-lactone, and the four hydroxyl groups of the glucose ring are substituted with benzyl groups. Additionally, a thiol group is attached to carbon 5 of the glucose ring. 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone is commonly used in organic synthesis as a protecting group for the hydroxyl groups in carbohydrates, and it can also be used as a precursor for the synthesis of other organic compounds. It is a white to off-white solid at room temperature and is sparingly soluble in water.

Upstream product

• 131757-84-1 methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 28585-88-8 methyl 5-deoxy-5-thio-α-D-glucopiranoside 
• 10227-17-5 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 10227-18-6 1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 102029-58-3 3-O-acetyl-6-O-benzoyl-1,2-O-isopropylidene-5-O-methylsulphonyl-α-D-glucofuranose 

Downstream Products

• 1019209-75-6 (1S,3'R,4'S,5'S,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-3',4',5',6'-tetrahydro-6-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]thiopyran] 
• 1415471-04-3 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((2,3-dihydrobenzorbiri,41dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-3,4,5-triol 
• 1221506-18-8 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-5-(4-ethylbenzyl)-2-methoxyphenyl]-5-thio-D-glucopyranose 
• 1221506-17-7 2,3,4,6-tetra-O-benzyl-1-C-[2-methoxy-4-methyl-5-[4-(propan-2-yl)benzyl]phenyl]-5-thio-D-glucopyranose 
• 1221506-16-6 2,3,4,6-tetra-O-benzyl-1-C-[5-(4-ethylbenzyl)-2-methoxy-4-methylphenyl]-5-thio-D-glucopyranose 
• 1221506-15-5 2,3,4,6-tetra-O-benzyl-1-C-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-5-thio-D-glucopyranose 
• 1221506-14-4 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-[4-(methylsulfanyl)benzyl]phenyl]-5-thio-D-glucopyranose 
• 1221506-12-2 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-[4-(propan-2-yl)benzyl]phenyl]-5-thio-D-glucopyranose 
• 1221506-10-0 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(4-methylbenzyl)phenyl]-5-thio-D-glucopyranose 
• 1221506-09-7 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(4-methoxybenzyl)phenyl]-5-thio-D-glucopyranose 
• 1221506-06-4 2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-(4-ethoxybenzyl)phenyl]-5-thio-D-glucopyranose 
• 1221505-98-1 2,3,4,6-tetra-O-benzyl-1-C-[3-(4-ethoxybenzyl)-4-fluorophenyl]-5-thio-D-glucopyranose 
• 1221505-97-0 2,3,4,6-tetra-O-benzyl-1-C-[3-(4-ethoxybenzyl)-4-methoxyphenyl]-5-thio-D-glucopyranose 
• 1221505-96-9 2,3,4,6-tetra-O-benzyl-1-C-[4-(benzyloxy)-3-(4-ethoxybenzyl)phenyl]-5-thio-D-glucopyranose 

Relevant articles and documents

(1 S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio- d -glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment

Derivatives of a novel scaffold, C-phenyl 1-thio-d-glucitol, were prepared and evaluated for sodium-dependent glucose cotransporter (SGLT) 2 and SGLT1 inhibition activities. Optimization of substituents on the aromatic rings afforded five compounds with potent and selective SGLT2 inhibition activities. The compounds were evaluated for in vitro human metabolic stability, human serum protein binding (SPB), and Caco-2 permeability. Of them, (1S)-1,5-anhydro-1-[5- (4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-d-glucitol (3p) exhibited potent SGLT2 inhibition activity (IC50 = 2.26 nM), with 1650-fold selectivity over SGLT1. Compound 3p showed good metabolic stability toward cryo-preserved human hepatic clearance, lower SPB, and moderate Caco-2 permeability. Since 3p should have acceptable human pharmacokinetics (PK) properties, it could be a clinical candidate for treating type 2 diabetes. We observed that compound 3p exhibits a blood glucose lowering effect, excellent urinary glucose excretion properties, and promising PK profiles in animals. Phase II clinical trials of 3p (TS-071) are currently ongoing.

1-PHENYL 1-THIO-D-GLUCITOL DERIVATIVE

A 1-phenyl 1-thio-D-glucitol compound represented by formula (I) or the like: or a pharmaceutically acceptable salt thereof or a hydrate thereof, or a pharmaceutical preparation comprising the same as an active ingredient is useful as a novel type of prophylactic or therapeutic agent for diabetes, diabetes-related diseases or diabetic complications, which inhibits both SGLT1 and SGLT2 activities to achieve not only suppression of glucose absorption from the digestive tract but also excretion of urinary sugars.

Synthesis of Per-O-alkylated 5-Thio-D-glucono-1,5-lactones and Transannular Participation of the Ring Sulphur Atom of 5-Thio-D-glucose Derivatives on Solvolysis under Acidic Conditions

Per-O-alkylated 5-thio-D-glucono-1,5-lactones (33)-(35) were synthesized via acetolysis or hydrolysis of the corresponding methyl glycosides (21)-(23).Transannular participation of the sulphur atom on acid methanolysis of 3,6-di-O-acetyl-5-S-acetyl-1,2-O-