(20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane

Base Information

• Chemical Name: (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane
• CAS No.: 65166-03-2
• Molecular Formula: C₂₃H₃₈O₂
• Molecular Weight: 346.554
• Mol file: 65166-03-2.mol

Synonyms:

Chemical Property of (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane

There total 9 articles about (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane 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: 85.0%

(20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregn-16-ene (101387-33-1) → (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane (51231-23-3,64681-80-7,64681-81-8,65166-03-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 5h; under 517.1 Torr;

Reference yield:

(17E)-6β-methoxy-3α,5-cyclo-5α-pregn-17(20)-en-16β-ol (84927-51-5) → (20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregnane (51231-23-3,64681-80-7,64681-81-8,65166-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) KH, 3.) t-BuLi / 1) THF, RT (4 h), reflux (1.5 h); 2) RT, 1.5 h, THF; 3) THF, 4 h, RT, reflux (30 min)

2: 85 percent / H₂ / Pd-C / ethyl acetate / 5 h / 517.1 Torr

With hydrogen; tert.-butyl lithium; potassium hydride; palladium on activated charcoal; In ethyl acetate;

Reference yield:

(Z)-21-(((bromomethyl)dimethylsilyl)oxy)-6β-methoxy-3α,5α-cyclopregn-17(20)-ene (119005-07-1) → 6β-methoxy-3α,5α-cyclobisnorcholan-22-ol (51231-23-3) + 6β-methoxy-3α,5α-cyclobisnorcholan-22-ol (65166-03-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; Yield given. Multistep reaction. Yields of byproduct given; 1a) benzene, 30min, reflux, 1b) RT, overnight, 2) DMSO, 100 deg C, 20h;

DOI:10.1021/jo00298a020

upstream raw materials:

4-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,2-dimethyl-[1,2]oxasilolane

(Z)-21-(((bromomethyl)dimethylsilyl)oxy)-6β-methoxy-3α,5α-cyclopregn-17(20)-ene

(E)-21-(((bromomethyl)dimethylsilyl)oxy)-6β-methoxy-3α,5α-cyclopregn-17(20)-ene

(20R)-20-hydroxymethyl-6β-methoxy-3α,5-cyclo-5α-pregn-16-ene

Downstream raw materials:

(20R)-3α,5α-cyclo-6β-methoxy-20(tosyloxymethyl)-pregrane

20-methylpregn-5-en-3β-ol