(3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one
• CAS No.: 90320-04-0
• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.612
• Mol file: 90320-04-0.mol

Synonyms:

Chemical Property of (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one

There total 21 articles about (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-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: 68.0%

(3R,5S)-5-((R)-2-((1R,3αR,7αR,E)-4-(bromomethylene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-methyl-3-((triethylsilyl)-oxy)dihydrofuran-2(3H)-one + (3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne (161055-41-0) → (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one (81203-50-1,75519-08-3,87680-15-7,90320-03-9,90320-04-0,95464-24-7,95464-25-8)

Guidance literature:

(3R,5S)-5-((R)-2-((1R,3αR,7αR,E)-4-(bromomethylene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-methyl-3-((triethylsilyl)-oxy)dihydrofuran-2(3H)-one; (3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In toluene; at 90 ℃; for 1h;

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 0 ℃; for 48h;

DOI:10.1021/acs.joc.9b00403

Reference yield: 39.0%

previtamin D3 → (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one (81203-50-1,75519-08-3,87680-15-7,90320-03-9,90320-04-0,95464-24-7,95464-25-8)

Guidance literature:

In ethanol; 1.) reflux, 45 min, 2.) 5 deg C, 10 d;

DOI:10.1021/jo00027a010

Reference yield:

Acetic acid (3aR,4R,7aS)-1-eth-(Z)-ylidene-7a-methyl-octahydro-inden-4-yl ester (81506-36-7) → (3R,5S)-5-((R)-2-((1R,3αS,7αR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one (81203-50-1,75519-08-3,87680-15-7,90320-03-9,90320-04-0,95464-24-7,95464-25-8)

Guidance literature:

Multi-step reaction with 10 steps

1: ethylaluminum dichloride / CH₂Cl₂ / 25 h / 0 deg C to room temp.

2: 91 percent / diisobutylaluminum hydride / tetrahydrofuran / 0 deg C to room temp.

3: 84 percent / KO-t-Bu / 2-methyl-propan-2-ol / Ambient temperature

4: 72 percent / H₂ / 5percent Pt on C / ethyl acetate

5: 99 percent / ethyl acetate / Ambient temperature

6: tetrahydrofuran / -78 deg C to room temp.

7: 2,2'-bipyridinium chlorochromate / CH₂Cl₂

9: 90 percent / tetrahydrofuran / -78 °C

10: ion exchange resin AG 50W-X₄, 200-400 mesh, H⁺-form, Bio-Rad Laboratories / methanol

With 200-400 mesh; Bio-Rad Laboratories; ion exchange resin AG 50W-X₄; potassium tert-butylate; hydrogen; ethylaluminum dichloride; hydrogen cation; diisobutylaluminium hydride; 2,2'-bipyridinium chlorochromate; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jo00171a068

upstream raw materials:

(3R,5S)-5-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-3-methyl-3-trimethylsilanyloxy-dihydro-furan-2-one

(23S,25R)-1α,3β,25-trihydroxy-5,7-cholestadiene 26,23-lactone

(23S,25R)-1α,3β,25-trihydroxy-5,7-cholestadiene 26,23-lactone 4-phenyl-1,2,4-triazoline-3,5-dione adduct

(22S,23R,25R)-1α,3β,25-trihydroxy-22-iodo-5,7-cholestadiene 26,23-lactone 4-phenyl-1,2,4-triazoline-3,5-dione adduct