3beta,11alpha,17-Trihydroxy-16alpha-methyl-5alpha-pregnan-20-one

Base Information

• Chemical Name: 3beta,11alpha,17-Trihydroxy-16alpha-methyl-5alpha-pregnan-20-one
• CAS No.: 1635-20-7
• Molecular Formula: C22H36 O4
• Molecular Weight: 364.525
• European Community (EC) Number: 216-658-9
• DSSTox Substance ID: DTXSID00936830
• Nikkaji Number: J195.267F
• Wikidata: Q82913041
• Mol file: 1635-20-7.mol

Synonyms:1635-20-7;3beta,11alpha,17-Trihydroxy-16alpha-methyl-5alpha-pregnan-20-one;EINECS 216-658-9;1-[(3S,5S,8S,9S,10S,11R,13S,14S,16R,17R)-3,11,17-trihydroxy-10,13,16-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone;5alpha-Pregnan-20-one, 3beta,11alpha,17-trihydroxy-16alpha-methyl-;DTXSID00936830;3,11,17-Trihydroxy-16-methylpregnan-20-one;Pregnan-20-one, 3,11,17-trihydroxy-16-methyl-, (3beta,5alpha,11alpha,16alpha)-

Chemical Property of 3beta,11alpha,17-Trihydroxy-16alpha-methyl-5alpha-pregnan-20-one

Chemical Property:

• Boiling Point: 509.4°Cat760mmHg
• Flash Point: 276°C
• PSA: 77.76000
• Density: 1.158g/cm³
• LogP: 2.92690
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 364.26135963
• Heavy Atom Count: 26
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4CC(CCC4(C3C(CC2(C1(C(=O)C)O)C)O)C)O
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@@]4([C@H]3[C@@H](C[C@@]2([C@]1(C(=O)C)O)C)O)C)O

Technology Process of 3beta,11alpha,17-Trihydroxy-16alpha-methyl-5alpha-pregnan-20-one

There total 11 articles about 3beta,11alpha,17-Trihydroxy-16alpha-methyl-5alpha-pregnan-20-one 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:

3β,11α-diacetoxy-17-hydroxy-16α-methyl-5α-pregnan-20-one (13263-45-1) → 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one (1635-20-7)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1002/hlca.19590420636

Reference yield:

3β,11α-diacetoxy-5α-pregn-16-en-20-one (28507-80-4) → 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one (1635-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: CuCl / anschliessende Acetylierung

2: monoperoxyphthalic acid; diethyl ether / Erwaermen des Reaktionsprodukts mit wss.-methanol.K₂CO₃ und Behandeln des danach isolierten Reaktionsprodukts mit Acetanhydrid und Pyridin

3: methanol; sodium methylate

With methanol; monoperoxyphthalic acid; diethyl ether; sodium methylate; copper(l) chloride;

DOI:10.1002/hlca.19590420636

Reference yield:

(17Ξ)-3β,11α,20-triacetoxy-16α-methyl-5α-pregn-17(20)-ene (810-38-8) → 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one (1635-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: monoperoxyphthalic acid; diethyl ether / Erwaermen des Reaktionsprodukts mit wss.-methanol.K₂CO₃ und Behandeln des danach isolierten Reaktionsprodukts mit Acetanhydrid und Pyridin

2: methanol; sodium methylate

With methanol; monoperoxyphthalic acid; diethyl ether; sodium methylate;

DOI:10.1002/hlca.19590420636

upstream raw materials:

3β,11α-diacetoxy-17-hydroxy-16α-methyl-5α-pregnan-20-one

3β,11α-diacetoxy-5α-pregn-16-en-20-one

(17Ξ)-3β,11α,20-triacetoxy-16α-methyl-5α-pregn-17(20)-ene

Downstream raw materials:

21-acetoxy-17-hydroxy-16α-methyl-5α-pregn-9(11)-ene-3,20-dione

21-acetoxy-17-hydroxy-16α-methyl-11α-(toluene-4-sulfonyloxy)-5α-pregnane-3,20-dione

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate