(2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran

Base Information

• Chemical Name: (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran
• CAS No.: 128574-68-5
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 128574-68-5.mol

Synonyms:(2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran

Chemical Property of (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran

There total 21 articles about (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran 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: 27.0%

(1RS,6S,7R)-6-Ethyl-1-(4-methoxyphenyl)octane-1,6,7-triol → (2S,5S)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran (128574-69-6) + (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran (128574-68-5)

Guidance literature:

(1S)-10-camphorsulfonic acid; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87184-2

Reference yield:

(4S,5R)-4,5-Dihydroxy-4-ethylhexanoic acid 1,4-lactone (151254-98-7) → (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran (128574-68-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / LiAlH₄ / diethyl ether / 5 h / 0 °C

2: 100 percent / CSA / 3 h / Ambient temperature

3: 94 percent / pyridinium chlorochromate, NaOAc, 3A molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 1) NaH / 1) THF, 20 min, r.t., 2) THF, 2 h, r.t.

5: 100 percent / NaBH₄, CeCl₃ / methanol / 0.17 h / 0 °C

6: 95 percent / d-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / Ambient temperature

7: 660 mg / Et₃N, 4-N,N-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

8: 1) d-camphorsulfonic acid, 2) LiAlH₄ / 1) CH₂Cl₂, r.t., 24 h, 2) Et₂O, 5 min

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; 3 A molecular sieve; camphor-10-sulfonic acid; (1S)-10-camphorsulfonic acid; sodium acetate; sodium hydride; triethylamine; pyridinium chlorochromate; (1S)-10-camphorsulfonic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)87184-2

Reference yield:

5-Deoxy-3-C-ethyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose → (2S,5R)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran (128574-68-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) NaH, 2) Et₂NH / 1) DMF, 7 h, r.t., 2) 5 h, r.t.

2: 99 percent / 4N HCl / tetrahydrofuran / 24 h / Ambient temperature

3: 97 percent / Pb(OAc)4 / benzene / 0.5 h / Ambient temperature

4: 77 percent / 1,2-dichloro-ethane / 24 h / 60 - 70 °C

5: 1) H₂, 2) K₂CO₃ / 1) 10percent Pd/C / 1) MeOH, 24 h, 2) 1 h

6: 100 percent / LiAlH₄ / diethyl ether / 5 h / 0 °C

7: 100 percent / CSA / 3 h / Ambient temperature

8: 94 percent / pyridinium chlorochromate, NaOAc, 3A molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

9: 1) NaH / 1) THF, 20 min, r.t., 2) THF, 2 h, r.t.

10: 100 percent / NaBH₄, CeCl₃ / methanol / 0.17 h / 0 °C

11: 95 percent / d-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / Ambient temperature

12: 660 mg / Et₃N, 4-N,N-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

13: 1) d-camphorsulfonic acid, 2) LiAlH₄ / 1) CH₂Cl₂, r.t., 24 h, 2) Et₂O, 5 min

With lead(IV) acetate; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; 3 A molecular sieve; camphor-10-sulfonic acid; (1S)-10-camphorsulfonic acid; hydrogen; sodium acetate; sodium hydride; potassium carbonate; diethylamine; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; (1S)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; benzene;

DOI:10.1016/S0040-4020(01)87184-2

upstream raw materials:

(E)-5-((4R,5R)-4-Ethyl-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-1-(4-methoxy-phenyl)-pent-2-en-1-ol

(E)-5-((4R,5R)-4-Ethyl-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-1-(4-methoxy-phenyl)-pent-1-en-3-ol

(2S,5S)-2-Ethyl-2-<(1R)-1-hydroxyethyl>-5-<(1E)-2-(4-methoxyphenyl)ethenyl>tetrahydrofuran

3-<(4S,5R)-4-Ethyl-2,2,5-trimethyl-1,3-dioxolan-4-yl>propanol

Downstream raw materials:

(2S,5R)-2-<(1R)-1-Benzyloxymethoxyethyl>-2-ethyl-5-formyltetrahydrofuran

(2R,3S,6R)-3-Ethyl-6-[(E)-2-(4-methoxy-phenyl)-vinyl]-2-methyl-tetrahydro-pyran-3-ol

Refernces

• 1、 Noda, Ichio,Horita, Kiyoshi,Oikawa, Yuji,Yonemitsu, Osamu. "SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANS AND TETRAHYDROPYRANS. 2. STEREOCONTROLLED ACID-CATALYZED CYCLIZATIONS". . p. 1917 - 1920. Retrieved 2007/10/02.