1461750-25-3

Basic information

• Product Name: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one
• Synonyms: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one
• CAS NO: 1461750-25-3
• Molecular Weight: 432.516
• Mol File: 1461750-25-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 585.4±50.0 °C(Predicted)
• Density: 1.19±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one(1461750-25-3)
• EPA Substance Registry System: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one(1461750-25-3)

Safety Data

• Hazardous Substances Data: 1461750-25-3(Hazardous Substances Data)

Usage

Description

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one is a complex organic molecule characterized by a tetrahydro-2H-pyran-2-one backbone, which is substituted with three benzyloxy groups and a methyl group. (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one features a chiral structure with four chiral centers, denoted by the R and S configurations. The presence of the benzyloxy groups introduces significant steric hindrance, which may influence the compound's reactivity and biological activity. The specific stereochemistry and functional groups of this molecule suggest potential applications in various fields, such as organic synthesis, medicinal chemistry, and materials science. However, further research and experimentation are required to fully comprehend its properties and potential uses.

Uses

Used in Organic Synthesis:
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one is used as an intermediate in organic synthesis for the development of complex molecular structures. Its unique stereochemistry and functional groups make it a valuable building block for creating novel compounds with specific properties and applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one is used as a potential candidate for drug discovery. Its specific stereochemistry and functional groups may allow for the design of new pharmaceuticals with targeted biological activities, potentially leading to the development of novel therapeutic agents.
Used in Materials Science:
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one may also find applications in materials science, where its unique structural features could be exploited to create new materials with specific properties. These materials could have potential uses in various industries, such as electronics, coatings, or adhesives.

Upstream product

• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 177078-61-4 (3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-iodomethyl-tetrahydro-pyran-2-one 
• 100-39-0 benzyl bromide 
• 1079205-73-4 C₃₇H₅₂O₆Si 
• 73111-14-5 3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran 
• 639504-92-0 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 1431771-67-3 (1S)-1,6-dideoxy-1-[4-methoxy-3-(trans-4-n-propylcyclohexyl)methylphenyl]-D-glucopyranose 

Relevant articles and documents

Synthesis method of Tilgliflozin intermediate

The invention belongs to the field of medicinal chemistry, and particularly relates to a synthesis method of a Tilgliflozin intermediate, which comprises the following steps: carrying out primary hydroxyl iodination and acetylation reaction on a compound A serving as a raw material to obtain iodinated acetate, reducing iodide into a methyl compound, preparing into a benzyl protection product, removing methyl protection, and reacting the swern oxidized hydroxyl in five steps to obtain a Tildagliflozin intermediate, namely a compound F. According to the method, the danger that in the prior art, due to the fact that selective silicon groups are adopted for protecting primary alcohol, benzyl is adopted for protecting three secondary alcohols, NaH is adopted, and consequently explosion is likely to happen is avoided, the reaction steps are further simplified, a high-yield final product can be obtained without column chromatography, and the total yield can reach 56%. The method provided by the invention is free of high-temperature and low-temperature reactions and dangerous reagents, the used raw materials are easy to obtain, the cost is greatly saved and is only 1/2-1/3 of that of a currently reported route, and the method has remarkable advantages.

Design, synthesis and biological evaluation of 6-deoxy O-spiroketal C-arylglucosides as novel renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

In this work, aiming at finding a novel, potent, and selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor with good pharmacokinetic profiles for the treatment of diabetes, we focus on modifying the sugar moiety of SGLT2 inhibitors, which dominates the binding with glucose binding site of hSGLT, via removing the C-6 hydroxy group to adjust the physicochemical properties and target-recognition manners of SGLT2 inhibitors. In addition, tofogliflozin containing a special O-spiroketal C-arylglucoside scaffold, displayed good efficacy and bioavailability both in animals and in humans. Therefore, a series of 6-deoxy O-spiroketal C-arylglucosides as novel SGLT2 inhibitors were designed, synthesized, and evaluated in this work. The structure-activity relationship (SAR) research on this novel series and a comprehensive in vitro and in vivo biological evaluation afforded compound 39 with high in vitro hSGLT2 inhibitory activity (IC50 = 4.5 nM), good pharmacokinetic profiles, and more remarkable efficacy in C57BL/6J mice and Sprague-Dawley rats than marketed drug tofogliflozin.

A 2, 3, 4 - c - O - benzyl - 6 - deoxy - D - pyran glucose acid - 1, 5 - lactone preparation method

The invention relates to a 2, 3, 4 - c - O - benzyl - 6 - deoxy - D - pyran glucose acid - 1, 5 - lactone of the preparation method, by 2, 3, 4 - c - O - benzyl - D - pyran methyl glucoside - 6 - a sulfonic acid ester obtained by the reaction of 2, 3, 4 - c - O - benzyl - 6 - iodo - D - pyran methyl glucoside, further by the reaction of the 2, 3, 4 - c - O - benzyl - 6 - deoxy - D - pyran methyl glucoside, further by the reaction of the 2, 3, 4 - c - O - benzyl - 6 - deoxy - D - pyran methyl glucose, the final reaction to make said 2, 3, 4 - c - O - benzyl - 6 - deoxy - D - pyran glucose acid - 1, 5 - lactone. The invention realizes the kg at the time of preparation, 2, 3, 4 - c - O - benzyl - 6 - deoxy - D - pyran glucose acid - 1, 5 - lactone of the yield and purity is still very high, is suitable for industrial production.