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

Base Information

• Chemical Name: (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole
• CAS No.: 115018-52-5
• Molecular Formula: C₂₅H₃₇NO₂
• Molecular Weight: 383.574
• Mol file: 115018-52-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole 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%

decylidenetriphenylphosphorane (79827-34-2) + (1R,2E,4'S)-5-formyl-1-(2'-phenyl-4',5'-dihydrooxazol-4'-yl)-2-penten-1-ol (262592-94-9) → (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole (115018-52-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -70 - 0 ℃;

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

Reference yield:

1-Bromononane (693-58-3) → (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole (115018-52-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-BuLi / 1.) n-hexane, THF, 1 h, -10 deg C, 2.) n-hexane, THF, HMPT, 11 h, room temperature

2: p-toluenesulfonic acid monohydrate / methanol / 18 h / Ambient temperature

3: 83 percent / H₂, quinoline / 5percent Pd/BaSO₄ / methanol / 760 Torr / Ambient temperature

4: pyridine / 9 h / 0 °C

5: dimethylsulfoxide / 18 h / Ambient temperature

6: 1.) (i-Bu)2AlH, 2.) tartaric acid / 1.) n-hexane, ether, 1 h, -20 deg C; 1 h, RT, 2.) n-hexane, ether, water, 1 h

7: 1.) triphenylphosphine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, 15 min, 0 deg C

8: 70 percent / n-BuLi / hexane; tetrahydrofuran / 1.) 30 min, -70 deg C, 2.) 1 h, room temperature

9: 1.) (i-Bu)2AlH / 1.) n-hexane, 3 h, 50 deg C, 2.) n-hexane, ether, toluene, 1,5 h, room temperature

With quinoline; n-butyllithium; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; tartaric acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; hexane; dimethyl sulfoxide;

Reference yield:

tridec-3-yn-1-ol (54373-82-9) → (4S,1'R,2'E,6'Z)-4,5-dihydro-4-(1'-hydroxy-2',6'-hexadecadienyl)-2-phenyl-1,3-oxazole (115018-52-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / H₂, quinoline / 5percent Pd/BaSO₄ / methanol / 760 Torr / Ambient temperature

2: pyridine / 9 h / 0 °C

3: dimethylsulfoxide / 18 h / Ambient temperature

4: 1.) (i-Bu)2AlH, 2.) tartaric acid / 1.) n-hexane, ether, 1 h, -20 deg C; 1 h, RT, 2.) n-hexane, ether, water, 1 h

5: 1.) triphenylphosphine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, 15 min, 0 deg C

6: 70 percent / n-BuLi / hexane; tetrahydrofuran / 1.) 30 min, -70 deg C, 2.) 1 h, room temperature

7: 1.) (i-Bu)2AlH / 1.) n-hexane, 3 h, 50 deg C, 2.) n-hexane, ether, toluene, 1,5 h, room temperature

With quinoline; n-butyllithium; hydrogen; diisobutylaluminium hydride; tartaric acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; hexane; dimethyl sulfoxide;

upstream raw materials:

4-formyl-2-phenyl-Δ²-oxazoline

(Z)-pentadec-5-en-1-yne

(E)-2-dodecenyl chloride

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

Downstream raw materials:

(2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-4,8-sphingadienine

(2S,3R,4E,8Z,2'R)-3-O-(tert-butyldiphenylsilyl)-N-(2'-hydroxyhexadecanoyl)-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-4,8-sphingadienine

(2S,3R,4E,8Z,2'R)-N-(2'-Acetoxyhexadecanoyl)-1-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-4,8-sphingadienine

(2S,3R,4E,8Z,2'R)-2-(2'-acetoxyhexadecanoyl)amino-3-O-acetyl-1-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,8-octadiene-1,3-diol