17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione

Base Information

• Chemical Name: 17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione
• CAS No.: 10184-69-7
• Molecular Formula: C21H26O4
• Molecular Weight: 342.435
• UNII: ZCF6ZW8234
• ChEMBL ID: CHEMBL2348783
• DSSTox Substance ID: DTXSID001234812
• Nikkaji Number: J516.134G
• Mol file: 10184-69-7.mol

Synonyms:Deltacortinene;10184-69-7;17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione;ZCF6ZW8234;Prednisone impurity D [EP];UNII-ZCF6ZW8234;Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-;(8S,10S,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one;SCHEMBL8200623;CHEMBL2348783;DTXSID001234812;PREDNISONE IMPURITY D [EP IMPURITY];17a,21-dihy-droxy-pregna-1,4,9(11)-triene-3,20-dione

Chemical Property of 17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 342.18310931
• Heavy Atom Count: 25
• Complexity: 745

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC=C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC43C
• Isomeric SMILES: C[C@]12CC=C3[C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)CCC4=CC(=O)C=C[C@@]43C

Technology Process of 17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione

There total 1 articles about 17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione 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:

anecortave (7753-60-8) → Anecortave (10184-70-0) + pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) + (10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one (10184-69-7) + pregna-1,4,9(11)-triene-17α,20β,21-triol-3-one

Guidance literature:

With Nocardioides simplex VKM Ac-2033D; In phosphate buffer; at 28 ℃; pH=7.5; Further Variations:; pH-values; Product distribution; Enzymatic reaction;

DOI:10.1016/S0039-128X(03)00043-6

Reference yield:

(10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one (10184-69-7) → prednisolon (50-24-8,8056-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap / chloroform / 0.17 h

1.2: 10 - 20 °C

2.1: sulfuric acid / acetone; water / 0.5 h / 0 - 5 °C

2.2: 0 - 5 °C

3.1: zinc; chromium(VI) oxide; mercaptoacetic acid / acetone; dimethyl sulfoxide / 15 - 20 °C

3.2: 1 h

3.3: 0.33 h

4.1: sodium hydroxide; potassium carbonate; water / methanol / 2 h / 0 - 10 °C / Inert atmosphere

With chromium(VI) oxide; dmap; sulfuric acid; water; potassium carbonate; mercaptoacetic acid; sodium hydroxide; zinc; In methanol; chloroform; water; dimethyl sulfoxide; acetone;

Reference yield:

(10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one (10184-69-7) → prednisolone 21-acetate (52-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap / chloroform / 0.17 h

1.2: 10 - 20 °C

2.1: sulfuric acid / acetone; water / 0.5 h / 0 - 5 °C

2.2: 0 - 5 °C

3.1: zinc; chromium(VI) oxide; mercaptoacetic acid / acetone; dimethyl sulfoxide / 15 - 20 °C

3.2: 1 h

3.3: 0.33 h

With chromium(VI) oxide; dmap; sulfuric acid; mercaptoacetic acid; zinc; In chloroform; water; dimethyl sulfoxide; acetone;

upstream raw materials:

anecortave

Downstream raw materials:

prednisolon

prednisolone 21-acetate

Refernces