(3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran

Base Information

• Chemical Name: (3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran
• CAS No.: 84751-58-6
• Molecular Formula: C₁₉H₂₆O₃S
• Molecular Weight: 334.48
• Mol file: 84751-58-6.mol

Synonyms:(3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran

Chemical Property of (3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran

There total 18 articles about (3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran 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:

thiophenol (108-98-5) + (E)-(2R,4R,6S)-2-(3-hexen-5-ynyl)tetrahydro-4,6-dimethoxy-2H-pyran (103438-16-0) → (2S,4R,6R)-2,4-Dimethoxy-6-((3E,5E)-6-phenylsulfanyl-hexa-3,5-dienyl)-tetrahydro-pyran (84751-58-6,84800-51-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In N,N,N,N,N,N-hexamethylphosphoric triamide; at 150 ℃; for 0.0833333h; Yield given;

DOI:10.1021/ja00343a072

Reference yield:

methyl 3,4-anhydro-2-deoxy-6-O-(triphenylmethyl)-α-D-ribo-hexopyranoside (73541-95-4) → (3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran (84751-58-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) lithium aluminum hydride, 2) sodium hydride (56.8percent oil dispersion) / 1) ether, -10 deg C, 3.5 h, 2) THF, RT, 18 h

2: 79 percent / sodium, ammonia / tetrahydrofuran / 1) -78 deg C, 30 min, 2) reflux, 30 min

3: 96 percent / pyridine / 11 h / Ambient temperature

4: 96 percent / sodium iodide / butan-2-one / 4 h / Heating; in dark

5: 90 percent / sodium hydride (56.8percent oil dispersion) / dimethylsulfoxide / 9 h

6: 92 percent / sodium phosphate, sodium amalgam / methanol / 0.25 h

7: 100 percent / lithium aluminum hydride / diethyl ether / 0.25 h

8: 90 percent / pyridine, chromium trioxide / CH₂Cl₂ / 0.33 h / 0 °C

9: 1) n-butyllithium, 2) tetrabutylammonium fluoride / 1) THF, hexane, RT, 1 h, 2) THF, 10 min

10: hexamethylphosphoramide, 2,2'-dimethyl-2,2'-azopropionitrile / 0.08 h

With pyridine; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; sodium phosphate; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; butanone;

DOI:10.1021/ja00279a041

Reference yield:

methyl 2,4-dideoxy-3-O-methyl-α-D-erythro-hexopyranoside (84751-44-0) → (3E)-(2S,4R,6R)-tetrahydro-2,4-dimethoxy-6-<6-(phenylthio)-3,5-hexadienyl>-2H-pyran (84751-58-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / pyridine / 11 h / Ambient temperature

2: 96 percent / sodium iodide / butan-2-one / 4 h / Heating; in dark

3: 90 percent / sodium hydride (56.8percent oil dispersion) / dimethylsulfoxide / 9 h

4: 92 percent / sodium phosphate, sodium amalgam / methanol / 0.25 h

5: 100 percent / lithium aluminum hydride / diethyl ether / 0.25 h

6: 90 percent / pyridine, chromium trioxide / CH₂Cl₂ / 0.33 h / 0 °C

7: 1) n-butyllithium, 2) tetrabutylammonium fluoride / 1) THF, hexane, RT, 1 h, 2) THF, 10 min

8: hexamethylphosphoramide, 2,2'-dimethyl-2,2'-azopropionitrile / 0.08 h

With pyridine; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; sodium hydride; sodium phosphate; sodium iodide; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; butanone;

DOI:10.1021/ja00279a041

upstream raw materials:

thiophenol

(E)-(2R,4R,6S)-2-(3-hexen-5-ynyl)tetrahydro-4,6-dimethoxy-2H-pyran

methyl 3,4-anhydro-2-deoxy-6-O-(triphenylmethyl)-α-D-ribo-hexopyranoside

(2S,4R,6S)-tetrahydro-2-(iodomethyl)-4,6-dimethoxy-2H-pyran

Refernces

• 1、 Grieco, Paul A.,Zelle, Robert E.,Lis, Randall,Finn, John. "Total Synthesis of the Hypochloesterolemic Agent (+)-Compactin". . p. 1403 - 1404. Retrieved 2007/10/02.