2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)propan-2-ol

Base Information

• Chemical Name: 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)propan-2-ol
• CAS No.: 213816-78-5
• Molecular Formula: C₂₆H₃₆O₄S
• Molecular Weight: 444.635
• Mol file: 213816-78-5.mol

Synonyms:2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)propan-2-ol

Chemical Property of 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)propan-2-ol

There total 41 articles about 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)propan-2-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: 86.0%

methyllithium (917-54-4) + 1-((E)-(1S,3R,5R,12S)-7-Benzenesulfonyl-1,5,9-trimethyl-4-oxa-tricyclo[10.3.0.03,5]pentadeca-8,13-dien-13-yl)-ethanone (213817-05-1) → 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.03,5]pentadeca-8,13-dien-13-yl)propan-2-ol (213816-78-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(98)01385-9

Reference yield:

(2E)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-2-buten-1-ol (162188-27-4) → 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.03,5]pentadeca-8,13-dien-13-yl)propan-2-ol (213816-78-5)

Guidance literature:

Multi-step reaction with 18 steps

1: 80 percent / N-bromosuccinimide; (C₆H₅)3P / CH₂Cl₂ / 2 h / 0 °C

2: (n-C₄H₉)Li / tetrahydrofuran; hexane / 0.67 h / -30 °C

3: 524 mg / Na; NH₃ / tetrahydrofuran / 1 h / -78 °C

4: pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 5 h / 20 °C

5: 3.70 g / C₆H₅Li / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / 0 °C

6: 85 percent / pyridinium chlorochromate; Al₂O₃ / benzene / 5 h / 40 °C

7: di(isobutyl)aluminum hydride / toluene; hexane / 0.17 h / -78 °C

8: 80 percent / NaH / tetrahydrofuran / 1 h / 0 °C

9: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10: 92 percent / (n-C₄H₉)3P; pyridine / 2 h / 60 °C

11: 90 percent / Oxone(R) / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

12: 98 percent / di(isobutyl)aluminum hydride / toluene; hexane / 0.25 h / -78 °C

13: 100 percent / D-diethyl tartrate; Ti(O-i-Pr)4; tert-butyl hydroperoxide / CH₂Cl₂ / 6 h / -20 °C

14: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 20 °C

15: 43 percent / ((CH₃)3Si)2N^(1-)*K⁽¹⁺⁾ / tetrahydrofuran; toluene / 1.5 h / 45 °C

16: 93 percent / CH₃COOH / H₂O / 0.5 h / 45 °C

17: 100 percent / K₂CO₃ / methanol / 1 h / 20 °C

18: 86 percent / tetrahydrofuran / 0.17 h / -78 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; aluminum oxide; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; oxone; diisobutylaluminum hydride; Diethyl tartrate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; sodium; potassium hexamethylsilazane; sodium hydride; potassium carbonate; acetic acid; phenyllithium; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; water; toluene; benzene; 13: Sharpless oxidation;

DOI:10.1016/S0040-4020(02)01474-6

Reference yield:

(E)-[(4-bromo-3-methylbut-2-en-1-yl)oxy](tert-butyl)dimethylsilane (213816-70-7) → 2-((1S,3R,5R,12S)-(E)-7-benzenesulfonyl-1,5,9-trimethyl-4-oxatricyclo[10.3.0.03,5]pentadeca-8,13-dien-13-yl)propan-2-ol (213816-78-5)

Guidance literature:

Multi-step reaction with 17 steps

1: (n-C₄H₉)Li / tetrahydrofuran; hexane / 0.67 h / -30 °C

2: 524 mg / Na; NH₃ / tetrahydrofuran / 1 h / -78 °C

3: pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 5 h / 20 °C

4: 3.70 g / C₆H₅Li / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / 0 °C

5: 85 percent / pyridinium chlorochromate; Al₂O₃ / benzene / 5 h / 40 °C

6: di(isobutyl)aluminum hydride / toluene; hexane / 0.17 h / -78 °C

7: 80 percent / NaH / tetrahydrofuran / 1 h / 0 °C

8: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9: 92 percent / (n-C₄H₉)3P; pyridine / 2 h / 60 °C

10: 90 percent / Oxone(R) / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

11: 98 percent / di(isobutyl)aluminum hydride / toluene; hexane / 0.25 h / -78 °C

12: 100 percent / D-diethyl tartrate; Ti(O-i-Pr)4; tert-butyl hydroperoxide / CH₂Cl₂ / 6 h / -20 °C

13: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1.5 h / 20 °C

14: 43 percent / ((CH₃)3Si)2N^(1-)*K⁽¹⁺⁾ / tetrahydrofuran; toluene / 1.5 h / 45 °C

15: 93 percent / CH₃COOH / H₂O / 0.5 h / 45 °C

16: 100 percent / K₂CO₃ / methanol / 1 h / 20 °C

17: 86 percent / tetrahydrofuran / 0.17 h / -78 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; aluminum oxide; dipyridinium dichromate; n-butyllithium; oxone; diisobutylaluminum hydride; Diethyl tartrate; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; sodium; potassium hexamethylsilazane; sodium hydride; potassium carbonate; acetic acid; phenyllithium; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; water; toluene; benzene; 12: Sharpless oxidation;

DOI:10.1016/S0040-4020(02)01474-6

upstream raw materials:

methyllithium

1-((E)-(1S,3R,5R,12S)-7-Benzenesulfonyl-1,5,9-trimethyl-4-oxa-tricyclo[10.3.0.0^3,5]pentadeca-8,13-dien-13-yl)-ethanone

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester

(2E)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-2-buten-1-ol

Downstream raw materials:

3R,4R-epoxy-13-keto-1R,11S-dolabell-7E,12⁽¹⁸⁾-diene