9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid

Base Information

• Chemical Name: 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid
• CAS No.: 37927-01-8
• Molecular Formula: C21H27 F O5
• Molecular Weight: 378.441
• Hs Code.: 9999999999
• Mol file: 37927-01-8.mol

Synonyms:(-)-Dexamethasoneacid; 9-Fluoro-11b,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17b-carboxylic acid

Chemical Property of 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 274-2770C
• Refractive Index: 1.598
• Boiling Point: 566.865°C at 760 mmHg
• PKA: 3.58±0.70(Predicted)
• Flash Point: 296.63°C
• PSA: 94.83000
• Density: 1.351g/cm³
• LogP: 2.41890
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

DexamethasoneAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A glucocorticoid receptor of spleen tumor of human, a steroid for inhibiting angiogenesis and tumor growth and treating ocular hypertension Dexamethasone Acid (Dexamethasone Sodium Phosphate EP Impurity G) is a glucocorticoid receptor of spleen tumor of human, a steroid for inhibiting angiogenesis and tumor growth and treating ocular hypertension.

Technology Process of 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid

There total 3 articles about 9-Fluoro-11,17-dihydroxy-16a-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid 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: 99.0%

dexamethasone (50-02-2) → (8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid (37927-01-8)

Guidance literature:

dexamethasone; With oxygen; potassium carbonate; In methanol; at 20 ℃; for 18h;

With hydrogenchloride; In water;

Reference yield:

dexamethasone (50-02-2) → (8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid (37927-01-8) + 17α-formyloxy-11β-hydroxy-9α-fluoro-16α-methyl-3-oxo-1,4-androstadien-17β-carboxylic acid (473273-04-0) + 9α-fluoro-11β,17α-dihydroxy-16α-methyl-3,20-dioxopregna-1,4-dien-21-oic acid

Guidance literature:

dexamethasone; With copper diacetate; air; for 1.5h;

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 25 - 40 ℃; for 16h;

DOI:10.1021/jo020282g

Reference yield:

dexamethasone glyoxal (2964-79-6) → (8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid (37927-01-8)

Guidance literature:

In various solvent(s); pH=9.2; Further Variations:; pH-values; Product distribution;

DOI:10.1016/j.steroids.2005.08.003

upstream raw materials:

dexamethasone

dexamethasone glyoxal

Downstream raw materials:

N-(2-(2-(2-((2-(biphenyl-4-ylmethyl)-3-(2,3-dihydroxypropyl)-3-isobutylisoxazolidin-5-yl)methylamino)-2-oxoethoxy)ethoxy)ethyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxamide

9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid [2-(2-{[(2-benzyl-3-(2,3-dihydroxy-propyl)-3-isobutyl-isoxazolidin-5-ylmethyl)-carbamoyl]-methoxy}-ethoxy)-ethyl]-amide

9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid [2-(2-{[4-benzylamino-2-hydroxy-4-(2-hydroxy-ethyl)-6-methyl-heptylcarbamoyl]-methoxy}-ethoxy)-ethyl]-amide

N-(2-(2-(2-((2-(biphenyl-4-ylmethyl)-3-(2-hydroxyethyl)-3-isobutylisoxazolidin-5-yl)methylamino)-2-oxoethoxy)ethoxy)ethyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxamide

Refernces

• 1、 Sau, Samaresh,Mondal, Sujan Kumar,Kashaw, Sushil K.,Iyer, Arun K.,Banerjee, Rajkumar. "Combination of cationic dexamethasone derivative and STAT3 inhibitor (WP1066) for aggressive melanoma: a strategy for repurposing a phase I clinical trial drug". . p. 119 - 136. Retrieved 2017.
• 2、 Kolbe, Adelheid,Kramell, Robert,Porzel, Andrea,Schmidt, Juergen,Schneider, Gernot,Adam, Guenter. "Syntheses of dexamethasone conjugates of the phytohormones gibberellin A3 and 24-epicastasterone". . p. 103 - 114. Retrieved 2002.
• 3、 Zhou, Min,Sivaramakrishnan, Ananthapadmanab,Ponnamperuma, Krishan,Low, Woon-Kai,Li, Chunmei,Liu, Jun O.,Bergbreiter, David E.,Romo, Daniel. "Synthesis, characterization, and utility of thermoresponsive natural/unnatural product macroligands for affinity chromatography". . p. 5247 - 5250. Retrieved 2006.
• 4、 -. "REGULATING CHIMERIC ANTIGEN RECEPTORS". Page/Page column 370. . Retrieved 2018/09/08.