86795-38-2

Basic information

• Product Name: 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside
• Synonyms: 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside
• CAS NO: 86795-38-2
• Molecular Weight: 434.532
• Mol File: 86795-38-2.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside(86795-38-2)
• EPA Substance Registry System: 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside(86795-38-2)

Safety Data

• Hazardous Substances Data: 86795-38-2(Hazardous Substances Data)

Usage

General Description

2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside is a chemical compound that belongs to the family of rhamnose derivatives. It is a trisaccharide, consisting of a rhamnose molecule with three phenylmethyl groups attached to its hydroxyl groups at positions 2, 3, and 4. 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside is commonly used in organic synthesis and chemical biology as a starting material for the preparation of various glycosides and other carbohydrate derivatives. Its unique structure and reactivity make it a valuable building block for the production of pharmaceuticals, natural products, and other complex organic compounds. Additionally, it has potential applications in medicinal chemistry and drug discovery due to its ability to modify the biological activity and properties of target molecules.

Upstream product

• 87-72-9 D-Xylose 
• 59055-57-1 methyl 2,3,4-tri-O-benzyl-α-L-rhamnopyranoside 
• 1338567-52-4 C₂₉H₃₁Cl₃O₅ 
• 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 
• 114219-26-0 methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside 
• 120449-27-6 Phosphoric acid dibenzyl ester (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester 
• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 6014-42-2 L-rhamnose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 153745-68-7 phenyl 1-thio-L-rhamnopyranoside 
• 153745-67-6 phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 

Downstream Products

• 2079-46-1 (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol 
• 1461750-25-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one 
• 104495-20-7 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride 
• 134312-02-0 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-6-methyl-tetrahydro-pyran 
• 134311-75-4 (2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-6-methyl-tetrahydro-pyran 
• 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 
• 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 
• 86795-41-7 p-aminophenyl 2-O-acetyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside 
• 103368-07-6 (3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 
• 103368-07-6 (3β,5β,14β,17β)-3β-<(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)oxy>-14-hydroxycard-20(22)-enolide 
• 508-93-0 digitoxigenin 3-(α-L-rhamnopyranoside) 
• 197916-18-0 (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate 
• 197916-09-9 allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside 
• 197916-17-9 (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 

Relevant articles and documents

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 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.

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.