(R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one

Base Information

• Chemical Name: (R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one
• CAS No.: 81239-84-1
• Molecular Formula: C₃₇H₅₁F₃O₅S
• Molecular Weight: 664.87
• Mol file: 81239-84-1.mol

Synonyms:(R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one

Chemical Property of (R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one

There total 1 articles about (R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-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: 78.0%

ethyl trifluoroacetate, (383-63-1) + 24-phenylsulphonylchol-5-en-3β-ol 3-tetrahydropyranyl ether (75303-40-1) → (R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one (81239-84-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1.5h;

DOI:10.1016/S0040-4039(01)82942-7

Reference yield:

(R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one (81239-84-1) → 27-nor-26,26,26-trifluoro-25-hydroxyvitamin D3 (81245-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Al-Hg 2.) NaBH₄ / 1.) aq. THF, reflux, 45 min 2.) THF, EtOH, room temp., 20 min

With sodium tetrahydroborate; aluminium amalgam;

DOI:10.1016/S0040-4039(01)82942-7

Reference yield:

(R)-3-Benzenesulfonyl-6-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1,1,1-trifluoro-heptan-2-one (81239-84-1) → Acetic acid (R)-5-{(1R,3aS,7aR)-4-[2-[(S)-5-acetoxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-1-trifluoromethyl-hexyl ester (81245-09-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Al-Hg 2.) NaBH₄ / 1.) aq. THF, reflux, 45 min 2.) THF, EtOH, room temp., 20 min

3: 1.) NBS 2.) s-collidine / 1.) CCl₄, reflux, 15 min. 2.) xylene, reflux, 10 min.

4: p-TsOH / acetone / 12 h

5: ethanol; benzene / 1 h / Heating; Irradiation

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; N-Bromosuccinimide; aluminium amalgam; toluene-4-sulfonic acid; In ethanol; acetone; benzene;

DOI:10.1016/S0040-4039(01)82942-7

upstream raw materials:

ethyl trifluoroacetate,

24-phenylsulphonylchol-5-en-3β-ol 3-tetrahydropyranyl ether

Downstream raw materials:

27-nor-26,26,26-trifluoro-25-hydroxyvitamin D₃

Acetic acid (R)-5-{(1R,3aS,7aR)-4-[2-[(S)-5-acetoxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-1-trifluoromethyl-hexyl ester