3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane

Base Information

• Chemical Name: 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane
• CAS No.: 81072-38-0
• Molecular Formula: C₃₈H₄₇NO₃
• Molecular Weight: 565.796
• Mol file: 81072-38-0.mol

Synonyms:3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane

Chemical Property of 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane

There total 12 articles about 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane 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: 80.0%

3β-(benzyloxy)-14β,15β-oxido-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane (83681-20-3) → 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane (81072-38-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -65 ℃; for 1h;

DOI:10.1021/jo00147a030

Reference yield: 52.0%

benzyl bromide (100-39-0) + (3S,5R,8R,9S,10S,13R,14S,17R)-3-Benzyloxy-17-(6-methoxy-pyridin-3-yl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-14-ol (81176-35-4) → 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane (81072-38-0)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Heating;

Reference yield:

2-methoxypyridine (1628-89-3) → 3β-(benzyloxy)-14β-hydroxy-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane (81072-38-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) butyllithium / 1.) Et₂O, -70 deg C, 2.) Et₂O

2: 91 percent / 4-dimethylaminopyridine / pyridine

3: 84 percent / CaCO₃ / acetone; H₂O / 48 h / Heating

4: 96 percent / H₂ / 10percent Pd/CaCO₃ / ethanol

5: 85 percent / methanesulfonyl chloride / pyridine

6: 1.) N-bromosuccinimide, 2.) alumina / 1.) H₂O, acetone, RT, 30 min, 2.) acetone, CH₂Cl₂

7: 74 percent / LiAlH₄ / tetrahydrofuran / Heating

8: 52 percent / potassium carbonate / acetone / 24 h / Heating

With dmap; aluminum oxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; hydrogen; potassium carbonate; methanesulfonyl chloride; calcium carbonate; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethanol; water; acetone;

upstream raw materials:

benzyl bromide

(3S,5R,8R,9S,10S,13R,14S,17R)-3-Benzyloxy-17-(6-methoxy-pyridin-3-yl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-14-ol

3β-(benzyloxy)-14β,15β-oxido-17β-<1-benzyl-2-hydroxy-5-pyridyl>-5β-androstane

2-methoxypyridine