[2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate

Base Information

• Chemical Name: [2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS No.: 1048031-82-8
• Molecular Formula: C24H32O6
• Molecular Weight: 416.51
• NSC Number: 63550
• UNII: AC9GRN27ZX
• Mol file: 1048031-82-8.mol

Synonyms:1048031-82-8;AC9GRN27ZX;[2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;2-((6R,8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-6,10,13-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate;UNII-AC9GRN27ZX;NSC63550;NSC-63550;6beta-Methyl prednisolone 21-acetate;Methyl prednisolone 21-acetate, 6beta-;Methylprednisolone acetate impurity J [EP];6.BETA.-METHYL PREDNISOLONE 21-ACETATE;METHYL PREDNISOLONE 21-ACETATE, 6.BETA.-;METHYLPREDNISOLONE ACETATE IMPURITY J [EP IMPURITY];11beta,17-Dihydroxy-6beta-methyl-3,20-dioxopregna-1,4-dien-21-yl acetate;11.BETA.,17-DIHYDROXY-6.BETA.-METHYL-3,20-DIOXOPREGNA-1,4-DIEN-21-YL ACETATE;Pregna-1,20-dione, 11.beta.,17,21-trihydroxy-6.beta.-methyl-, 21-acetate;Pregna-1,20-dione, 21-(acetyloxy)-11,17-dihydroxy-6-methyl-, (6.beta.,11.beta.)-;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-6-methyl-, (6beta,11beta)-;(6.BETA.,11.BETA.)-21-(ACETYLOXY)-11,17-DIHYDROXY-6-METHYLPREGNA-1,4-DIENE-3,20-DIONE;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-6-methyl-, (6.beta.,11.beta.)-

Chemical Property of [2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate

Chemical Property:

• Boiling Point: 582.5±50.0 °C(Predicted)
• PKA: 12.41±0.70(Predicted)
• PSA: 100.90000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 2.37440
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 416.21988874
• Heavy Atom Count: 30
• Complexity: 858

Purity/Quality:

98% ^*data from raw suppliers

6β-ΜethylPrednisolone21-Acetate(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)COC(=O)C)O
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)C)O)C)(C(=O)COC(=O)C)O
• Uses: 6β-Μethyl Prednisolone 21-Acetate is the 6-methyl isomer of 6α-Methyl Prednisolone 21-Acetate (M326030).

Technology Process of [2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate

There total 27 articles about [2-[(6R,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate 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:

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6) + acetic acid (64-19-7,77671-22-8) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione; With iodine; calcium oxide; In methanol; dichloromethane;

acetic acid; With potassium acetate; In acetone; at 45 - 50 ℃; for 2h;

Reference yield:

21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one (1968-76-9) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; tert-butyl alcohol; Reagens 4: Pyridin;

DOI:10.1021/ja01604a078

Reference yield:

17,21-dihydroxy-pregn-4-ene-3,11,20-trione (53-06-5,10007-36-0,15779-07-4,35446-72-1,104713-00-0) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

Multi-step reaction with 10 steps

1: aqueous hydrochloric acid; chloroform

2: benzene; toluene-4-sulfonic acid

3: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge

4: toluene-4-sulfonic acid

5: benzene; diethyl ether

6: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol

7: acetone; toluene-4-sulfonic acid

8: acetic acid; tert-butyl alcohol; selenium dioxide

9: aqueous formic acid

10: pyridine

With pyridine; hydrogenchloride; formic acid; selenium(IV) oxide; thionyl chloride; Perbenzoic acid; diethyl ether; chloroform; toluene-4-sulfonic acid; acetic acid; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/ja01514a055

upstream raw materials:

21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one

Methylprednisolone

acetic anhydride

17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

Downstream raw materials:

17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione

21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione

9,21-difluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione

9-fluoro-11β,17,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione