(1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol

Base Information

• Chemical Name: (1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol
• CAS No.: 262592-87-0
• Molecular Formula: C₁₆H₁₉NO₂
• Molecular Weight: 257.332
• Mol file: 262592-87-0.mol

Synonyms:(1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol

Chemical Property of (1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol

There total 1 articles about (1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol 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%

(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole (173531-24-3) + allylmagnesium bromide (1730-25-2) → (1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol (262592-87-0)

Guidance literature:

With CuCN; In diethyl ether; at -70 - -20 ℃;

DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

(1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol (262592-87-0) → soya-cerebroside II (115074-93-6)

Guidance literature:

Multi-step reaction with 9 steps

2: 145 mg / aq. HCl / tetrahydrofuran / 16 h / 20 °C

3: 198 mg / Et₃N / dimethylformamide / 6 h / 60 °C

4: 94 percent / NaOMe / CH₂Cl₂; methanol / 1 h / 0 °C

5: 91 percent / imidazole / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

6: 140 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 5 - 10 °C

7: 91 mg / AcOH; TBAF / tetrahydrofuran / 3 h / 20 °C

8: 77 percent / molecular sieves 4A; AgOTf / CH₂Cl₂; toluene / 2 h / -20 - 0 °C

9: 90 percent / NaOMe / tetrahydrofuran; methanol / 2 h / 5 - 10 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Ring cleavage / 3: Acylation / 4: Hydrolysis / 5: Substitution / 6: Acetylation / 7: Substitution / 8: Substitution / 9: Hydrolysis;

DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

(E)-2-dodecenyl chloride (71518-12-2) + (1R,2E,4'S)-1-(2'-phenyl-4',5'-dihdyrooxazol-4'-yl)hepta-2,6-dien-1-ol (262592-87-0) → (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole (115018-52-5) + (4S,1'R,2'E,6'E)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole (115018-42-3)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(99)01018-2

upstream raw materials:

(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole

allylmagnesium bromide

Downstream raw materials:

(4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole

(4S,1'R,2'E,6'E)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole

soya-cerebroside II