3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Base Information

• Chemical Name: 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS No.: 630-60-4
• Deprecated CAS: 36-06-6
• Molecular Formula: C29H44O12
• Molecular Weight: 584.661
• European Community (EC) Number: 211-139-3
• UN Number: 1544,1851
• Nikkaji Number: J15.724D
• Wikidata: Q63409494
• Wikipedia: Ouabain
• Mol file: 630-60-4.mol

Synonyms:630-60-4;Q63409494

Chemical Property of 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Chemical Property:

• Appearance/Colour: Odorless, white crystals or crystalline powder as an octahydrate
• Vapor Pressure: 7.63E-08mmHg at 25°C
• Melting Point: 200°C
• Refractive Index: -32 ° (C=1, H2O)
• Boiling Point: 838.219 °C at 760 mmHg
• PKA: 13.04±0.70(Predicted)
• Flash Point: 272.893 °C
• PSA: 206.60000
• Density: 1.52 g/cm³
• LogP: -1.51500
• Storage Temp.: Desiccate at -20°C
• Solubility.: H2O: 10 mg/mL cold
• Water Solubility.: 13g/L(25 oC)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 584.28327683
• Heavy Atom Count: 41
• Complexity: 1080
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Ouabain ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/25-33
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2CC(C3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
• Description: One of several cardiac glycosides that have been used clinically as cardiotonic agents and diuretics. Ouabain is obtained from the seeds of Strophanthus gratus, Acokanthera ouabaio, and related species. It was formerly prescribed under the name strophanthuis as the purified seed extract.

Technology Process of 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

There total 1 articles about 3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

C52H58O16 (1018988-68-5) → ouabain (630-60-4)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1002/anie.200704959

Reference yield: 88.0%

ouabain (630-60-4) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide (292068-65-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1.5h;

DOI:10.1016/S0039-128X(00)00096-9

Reference yield: 65.0%

ouabain (630-60-4) → dihydro-ouabain (1183-35-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen;

DOI:10.1021/cb500665r

upstream raw materials:

C₅₂H₅₈O₁₆

Downstream raw materials:

dihydro-ouabain

3',19-di-[(triisopropylsilyl)oxy]-3β-[(α-L-rhamnopyranosyl)oxy]-1β,5,11α,14-tetrahydroxycard-20(22)-enolide

C₄₃H₄₅F₅O₁₇S

ouabagenin

Refernces

Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin

10.1021/jo005712m

The study focuses on the solid-phase synthesis of O-Linked Glycopeptide Analogues of Enkephalin, which are peptide opiates designed to investigate the role of glycoside moieties and carbohydrate-peptide linkage regions in blood-brain barrier transport, opiate receptor binding, and analgesia. The researchers synthesized 18 N-R-FMOC-amino acid glycosides using Hanessian's modification of the Koenigs-Knorr reaction, incorporating various monosaccharides and disaccharides into 22 enkephalin glycopeptide analogues. These glycosides served as building blocks for the glycopeptides, which were assembled on Rink resin using FMOC peptide strategy. The study also explored the impact of different protecting groups and aglycone/glycosyl bromide pairs on the glycosylation yields and selectivity, optimizing the synthesis process for the glycopeptides. The chemicals used in the study include various amino acids, glycosyl bromides, protecting agents, and resins, all serving specific roles in the synthesis and protection of the glycopeptides during assembly.

Scope of AuCl₃ in the activation of per-O-acetylglycals

10.1016/j.tet.2009.07.087

The research investigates the application of AuCl3 as a catalyst in the activation of per-O-acetylglycals and its subsequent use in the Ferrier reaction to produce 2,3-unsaturated glycosides. The study demonstrates that AuCl3 efficiently activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal, enabling the Ferrier reaction with various nucleophiles at ambient conditions. The research also explores the potential of AuCl3 to influence the selectivity towards the formation of β-anomers, which are typically challenging to synthesize due to the anomeric effect. Key chemicals involved in the study include AuCl3 as the catalyst, per-O-acetylglycals such as 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal as the substrates, and a range of nucleophiles like primary, secondary, allylic, benzylic, and propargylic alcohols, as well as thiol and C-nucleophiles. The study also examines the use of additives like AgSbF6, AgOTf, and LiClO4 in attempts to enhance the β-selectivity of the reactions.

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