21-Deacetyldeflazacort

Base Information

• Chemical Name: 21-Deacetyldeflazacort
• CAS No.: 13649-57-5
• Deprecated CAS: 94158-00-6
• Molecular Formula: C₂₃H₂₉NO₅
• Molecular Weight: 399.487
• UNII: T1LWN33J2P
• DSSTox Substance ID: DTXSID201043063
• Nikkaji Number: J607.486C
• Wikidata: Q82887470
• Mol file: 13649-57-5.mol

Synonyms:21-deacetyldeflazacort;21-deacetyldeflazacort, (11beta,16beta)-isomer, 2'-(14)C-labeled;21-desacetyl-deflazacort;21-hydroxy-deflazacort;21-hydroxy-DF;21-hydroxydeflazacort;L 6485;L-6485

Chemical Property of 21-Deacetyldeflazacort

Chemical Property:

• Melting Point: 228-230°C
• Refractive Index: 1.69
• Boiling Point: 585°Cat760mmHg
• PKA: 12.88±0.10(Predicted)
• Flash Point: 307.6°C
• PSA: 96.19000
• Density: 1.45g/cm³
• LogP: 1.42800
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 399.20457303
• Heavy Atom Count: 29
• Complexity: 890

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

21-DesacetylDeflazacort ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2(C(O1)CC3C2(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)C(=O)CO
• Isomeric SMILES: CC1=N[C@@]2([C@H](O1)C[C@@H]3[C@@]2(C[C@@H]([C@H]4[C@H]3CCC5=CC(=O)C=C[C@]45C)O)C)C(=O)CO
• Uses: A metabolite of Deflazacort, a systemic corticosteroid, a derivative of prednisolone and used for rheumatoid arthritis and lupus. As a metabolite of Deflazacort, 21-Desacetyl Deflazacort can be used as a systemic corticosteroid, a derivative of prednisolone and used for rheumatoid arthritis and lupus.

Technology Process of 21-Deacetyldeflazacort

There total 20 articles about 21-Deacetyldeflazacort 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:

C23H28BrNO5 → 21-Deacetyldeflazacort (13649-57-5,94158-00-6)

Guidance literature:

With hydrogenchloride; chromium chloride; mercaptoacetic acid; In ethanol; water; at 20 ℃; for 0.5h; Reagent/catalyst; Green chemistry;

Reference yield:

deflazacort (14484-47-0) → 21-Deacetyldeflazacort (13649-57-5,94158-00-6)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/0039-128X(69)90046-4

Reference yield:

3β-hydroxy-2'-methyl-(5α,16β)-pregn-9(11)-eno[17,16-d]oxazol-20-one (19890-69-8) → 21-Deacetyldeflazacort (13649-57-5,94158-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1: (i) I₂, CaO, AIBN, THF, MeOH, (ii) /BRN= 506007/, Et₃N, acetone

2: aq. CrO₃ / acetone

3: (i) Br₂, aq. HBr, AcOH, dioxane, (ii) LiBr, Li₂CO₃, DMF

4: (i) AcNHBr, HClO₄, THF, (ii) Cr(OAc)2, nBuSH, DMSO

5: aq. NaOH / methanol

With chromium(VI) oxide; sodium hydroxide; In methanol; acetone;

DOI:10.1016/0039-128X(69)90046-4

upstream raw materials:

deflazacort

3β-hydroxy-2'-methyl-(5α,16β)-pregn-9(11)-eno[17,16-d]oxazol-20-one

3β-acetoxy-11β-hydroxy-2'-methyl-(5α,16β)-pregnano[17,16-d]oxazol-20-one

3β-acetoxy-2'-methyl-(5α,16β)-pregn-9(11)-eno[17,16-d]oxazol-20-one

Downstream raw materials:

deflazacort

Refernces

• 1、 -. "Preparation method of deflazacort". . . Retrieved 2017/08/27.