(+/-)-bilobalide

Base Information

Chemical Name:(+/-)-bilobalide
CAS No.:111554-25-7
Molecular Formula:C₁₅H₁₈O₈
Molecular Weight:326.303
Hs Code.:

Synonyms:

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Chemical Property of (+/-)-bilobalide

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-bilobalide

There total 25 articles about (+/-)-bilobalide 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: 70.0%

: 33570-05-7,111554-27-9
(+/-)-bilobalide 6-acetate

: 33570-04-6,111554-25-7
(+/-)-bilobalide

Guidance literature:: With hydrogenchloride; for 36h; Heating;
DOI:10.1021/ja00258a050

Reference yield:

: 917-92-0
3,3-Dimethylbut-1-yne

: 33570-04-6,111554-25-7
(+/-)-bilobalide

Guidance literature:: Multi-step reaction with 23 steps

1: n-butyllithium / diethyl ether / -20 °C

2: 72 percent / hexamethylphosphoric triamide / tetrahydrofuran / -45 deg C, 30 min, 0 deg C, 4 h

3: 75 percent / sodium borohydride / methanol; propan-2-ol / 7 h / 0 °C

4: 1.) O₃, sodium bicarbonate, 2.) dimethyl sulfide / 1.) -78 deg C, methylen chloride, methanol, 2.) methylen chloride, methanol

5: 72 percent / p-toluenesulfonic acid / 24 h / 23 °C

6: lithium aluminum hydride / diethyl ether / 1 h / 0 °C

7: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene chloride, -45 deg C, 2.) methylene chloride, 23 deg C

8: 1percent 1N HCl / tetrahydrofuran / 1 h / 0 °C

9: 80 percent / pyridinium dichromate, acetic acid, 4A molecular sieves / CH₂Cl₂ / 5 h / 23 °C

10: 90 percent / 1N potassium hydroxide / H₂O; tetrahydrofuran; ethanol / 12 h / 23 °C

11: methanesulfonyl chloride, triethylamine / -30 deg C, 30 min, 23 deg C, 2 h

12: diisopropylethylamine / acetonitrile / 12 h / Heating

13: 95 percent / peroxy-3,5-dinitrobenzoic acid, sodium bicarbonate / CH₂Cl₂ / 36 h / 23 °C

14: 0.5N HCl, H₂O / tetrahydrofuran / 3 h / 60 °C

15: 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 23 °C

16: 92 percent / peroxy-3-chlorobenzoic acid, boron trifluoride etherate / CH₂Cl₂; diethyl ether / 12 h / 60 °C

17: 0.5 N HCl, acetic acid / tetrahydrofuran / 3 h / 80 °C

18: pyridinium dichromate / CH₂Cl₂ / 4 h / 23 °C

19: 90 percent / triethylsilane / toluene / 36 h / 300 °C

20: osmium tetroxide, pyridine / diethyl ether / 12 h / 23 °C

21: 100 percent / diisopropylethylamine / acetonitrile / 2 h / 0 °C

22: 55 percent / 0.05M tri-n-butyltin hydride, azobisisobutyronitrile / toluene / Heating

23: 70 percent / 3N HCl / 36 h / Heating

With pyridine; hydrogenchloride; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; oxalyl dichloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; 3,5-dinitrobenzoperoxoic acid; boron trifluoride diethyl etherate; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;
DOI:10.1021/ja00258a050

Reference yield:

: 111436-86-3
phenyl 3-tert-butylpropiolate

: 33570-04-6,111554-25-7
(+/-)-bilobalide

Guidance literature:: Multi-step reaction with 22 steps

1: 72 percent / hexamethylphosphoric triamide / tetrahydrofuran / -45 deg C, 30 min, 0 deg C, 4 h

2: 75 percent / sodium borohydride / methanol; propan-2-ol / 7 h / 0 °C

3: 1.) O₃, sodium bicarbonate, 2.) dimethyl sulfide / 1.) -78 deg C, methylen chloride, methanol, 2.) methylen chloride, methanol

4: 72 percent / p-toluenesulfonic acid / 24 h / 23 °C

5: lithium aluminum hydride / diethyl ether / 1 h / 0 °C

6: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene chloride, -45 deg C, 2.) methylene chloride, 23 deg C

7: 1percent 1N HCl / tetrahydrofuran / 1 h / 0 °C

8: 80 percent / pyridinium dichromate, acetic acid, 4A molecular sieves / CH₂Cl₂ / 5 h / 23 °C

9: 90 percent / 1N potassium hydroxide / H₂O; tetrahydrofuran; ethanol / 12 h / 23 °C

10: methanesulfonyl chloride, triethylamine / -30 deg C, 30 min, 23 deg C, 2 h

11: diisopropylethylamine / acetonitrile / 12 h / Heating

12: 95 percent / peroxy-3,5-dinitrobenzoic acid, sodium bicarbonate / CH₂Cl₂ / 36 h / 23 °C

13: 0.5N HCl, H₂O / tetrahydrofuran / 3 h / 60 °C

14: 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 23 °C

15: 92 percent / peroxy-3-chlorobenzoic acid, boron trifluoride etherate / CH₂Cl₂; diethyl ether / 12 h / 60 °C

16: 0.5 N HCl, acetic acid / tetrahydrofuran / 3 h / 80 °C

17: pyridinium dichromate / CH₂Cl₂ / 4 h / 23 °C

18: 90 percent / triethylsilane / toluene / 36 h / 300 °C

19: osmium tetroxide, pyridine / diethyl ether / 12 h / 23 °C

20: 100 percent / diisopropylethylamine / acetonitrile / 2 h / 0 °C

21: 55 percent / 0.05M tri-n-butyltin hydride, azobisisobutyronitrile / toluene / Heating

22: 70 percent / 3N HCl / 36 h / Heating

With pyridine; hydrogenchloride; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; 3,5-dinitrobenzoperoxoic acid; boron trifluoride diethyl etherate; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;
DOI:10.1021/ja00258a050