86795-38-2

Usage

Uses

Used in Organic Synthesis:
2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside is used as a starting material for the preparation of various glycosides and other carbohydrate derivatives. Its unique structure allows for the creation of complex organic compounds, making it a valuable resource in this field.
Used in Chemical Biology:
In chemical biology, 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside is used as a building block for the production of pharmaceuticals and natural products. Its ability to modify the biological activity and properties of target molecules makes it a promising candidate for drug discovery and development.
Used in Medicinal Chemistry:
2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside is used in medicinal chemistry for its potential applications in drug discovery. Its unique structure and reactivity enable the modification of target molecules, which can lead to the development of new pharmaceuticals with improved biological activity and properties.

Upstream product

• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 120449-27-6 Phosphoric acid dibenzyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester 
• 100-39-0 benzyl bromide 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 77453-63-5 2,3,4-tri-O-benzyl-6-deoxy-D-iditol 
• 87-72-9 D-Xylose 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 77453-66-8 3,4,5-tri-O-benzyl-1-deoxy-α-D-sorbopyranose 
• 242143-00-6 methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 
• 59055-57-1 methyl 2,3,4-tri-O-benzyl-α-L-rhamnopyranoside 
• 100-44-7 benzyl chloride 
• 1338567-52-4 C₂₉H₃₁Cl₃O₅ 
• 73-34-7 L-rhamnose 
• 153745-67-6 phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 

Downstream Products

• 134312-01-9 3,5-Dinitro-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyridine 
• 134311-74-3 3,5-Dinitro-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyridine 
• 83866-10-8 2,2,2-Trichloro-acetimidic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester 
• 120449-25-4 O-(2,3,4-Tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) trichloroacetimidate 
• 177696-63-8 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl bromide 
• 142656-98-2 tert-Butyldimethylsilyl O-(2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1-4)-<(2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranosyl)-(1-2)>-3-O-benzyl-β-D-xylopyranoside 
• 1461750-25-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one 
• 2079-46-1 (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol 
• 103383-31-9 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose 
• 120269-13-8 O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->1)-2,3,4-tri-O-benzyl-α-L-rhamnopyranoside 
• 83866-10-8 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate 
• 103368-09-8 2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate 
• 104495-20-7 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride 
• 86795-40-6 p-nitrophenyl 2-O-acetyl-4-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

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.

Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides

A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.

Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds

Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.

PHENYL C-GLUCOSIDE DERIVATIVE CONTAINING DEOXYGLUCOSE STRUCTURE, PREPARATION METHOD AND USE THEREOF

The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicament

SrCl2 as an efficient cocatalyst for acidic hydrolysis of methyl glycosides

SrCl2 was found to be the most efficient cocatalyst for the acidic hydrolysis of methyl glycosides after 26 kinds of most representative metal salts were screened. The SrCl2-cocatalyzed acidic hydrolysis of methyl glycosides is highl

A facile synthesis of 6-deoxydapagliflozin

A facile synthesis of a potent SGLT2 inhibitor, 6-deoxydapagliflozin, from methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-d-glucopyranoside in six steps with an overall yield of 50 % is described. The key steps were the reductive deiodination of the starting

A highly efficient deprotection of the 2,2,2-trichloroethyl group at the anomeric oxygen of carbohydrates

Commercially available zinc dust in the presence of ammonium chloride in acetonitrile at reflux removes the 2,2,2-trichloroethyl (TCE) group at anomeric centers with excellent yields (>95%) in short reaction times. This present method is easily implemented on substrates containing acyl and benzyl groups and large-scale reactions also proceed in high yield.