Pregn-4-ene-3,20-dione, 11,17,18,21-tetrahydroxy-, (11beta)-

Base Information

• Chemical Name: Pregn-4-ene-3,20-dione, 11,17,18,21-tetrahydroxy-, (11beta)-
• CAS No.: 144302-17-0
• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.466
• UNII: T8YUY43659
• Nikkaji Number: J509.131D
• Mol file: 144302-17-0.mol

Synonyms:18-hydroxycortisol

Chemical Property of Pregn-4-ene-3,20-dione, 11,17,18,21-tetrahydroxy-, (11beta)-

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 378.20423867
• Heavy Atom Count: 27
• Complexity: 720

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC45C3CCC4(C(OC5)(CO)O)O)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@@]45[C@H]3CC[C@@]4([C@](OC5)(CO)O)O)O

Technology Process of Pregn-4-ene-3,20-dione, 11,17,18,21-tetrahydroxy-, (11beta)-

There total 5 articles about Pregn-4-ene-3,20-dione, 11,17,18,21-tetrahydroxy-, (11beta)- 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: 89.5%

18,20-epoxy-11β,20β-dihydroxy-17α,21-isopropylidenedioxypregn-4-en-3-one (144268-76-8) → 18,20-epoxy-11β,17α,20β,21-tetrahydroxypregn-4-ene-3-one (144302-17-0,81705-06-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 1.5h;

DOI:10.1016/0039-128X(92)90095-Q

Reference yield:

17α,21-(Dimethyl-methylendioxy)-Δ4-pregnenol-(11β)-dion-(3,20) (34332-34-8) → 18,20-epoxy-11β,17α,20β,21-tetrahydroxypregn-4-ene-3-one (144302-17-0,81705-06-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / I₂, lead tetraacetate, calcium carbonate / benzene; cyclohexane / 2 h / Irradiation

2: 82 percent / Jones reagent / acetone; CH₂Cl₂ / 0.33 h / 5 °C

3: 80 percent / silver acetate / dioxane; H₂O / 4 h / Heating

4: DDQ / dioxane / 18 h / Ambient temperature

5: 89.5 percent / HCl / tetrahydrofuran / 1.5 h

With lead(IV) acetate; hydrogenchloride; jones reagent; iodine; silver(I) acetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; water; acetone; benzene;

DOI:10.1016/0039-128X(92)90095-Q

Reference yield:

11β-hydroxy-18-iodo-17α,21-isopropylidenedioxypregn-4-ene-3,20-dione (144268-70-2) → 18,20-epoxy-11β,17α,20β,21-tetrahydroxypregn-4-ene-3-one (144302-17-0,81705-06-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Jones reagent / acetone; CH₂Cl₂ / 0.33 h / 5 °C

2: 80 percent / silver acetate / dioxane; H₂O / 4 h / Heating

3: DDQ / dioxane / 18 h / Ambient temperature

4: 89.5 percent / HCl / tetrahydrofuran / 1.5 h

With hydrogenchloride; jones reagent; silver(I) acetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1016/0039-128X(92)90095-Q

upstream raw materials:

18,20-epoxy-11β,20β-dihydroxy-17α,21-isopropylidenedioxypregn-4-en-3-one

17α,21-(Dimethyl-methylendioxy)-Δ⁴-pregnenol-(11β)-dion-(3,20)

11β-hydroxy-18-iodo-17α,21-isopropylidenedioxypregn-4-ene-3,20-dione

18,20-epoxy-20β-hydroxy-17α,21-isopropylidenedioxypregn-4-ene-3,20-dione