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

• 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 
• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose 
• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-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

Synthetic method of SGLT2 inhibitor intermediate

The invention discloses a synthesis method of an SGLT2 inhibitor intermediate, which comprises the following steps: S1, oxidation: dissolving a compound I, adding into an oxidation system, carrying out liquid-liquid separation, and collecting an organic phase A to obtain a compound II; S2, dealkylation: adding the compound II into a dealkylation system to obtain a reaction solution, and performing liquid-liquid separation to obtain a compound III; S3, iodination: adding the compound III into an iodination system, performing liquid-liquid separation, and collecting an organic phase B to obtain a compound IV; S4, reduction: dissolving the compound IV, adding the dissolved compound IV into a reduction system, carrying out liquid-liquid separation, and collecting an organic phase C to obtain a target product V; the synthesis method has few synthesis steps, and the process is simple and easy to operate; expensive and dangerous compounds are not used in the synthesis process, and no safety risk exists; the total yield reaches 60 percent or higher; the method uses commercially available starting materials, is low in cost, ensures good reproducibility of a synthetic route, and is a process suitable for large-scale industrial production.

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.