Kauran-20-oic acid,16,18-dihydroxy-, d-lactone, (4a)-

Base Information

• Chemical Name: Kauran-20-oic acid,16,18-dihydroxy-, d-lactone, (4a)-
• CAS No.: 149249-32-1
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Mol file: 149249-32-1.mol

Synonyms:1H,3H-6a,9-Methano-4,11b-propanocyclohepta[h][2]benzopyran,kauran-20-oic acid deriv.; Neotripterifordin

Chemical Property of Kauran-20-oic acid,16,18-dihydroxy-, d-lactone, (4a)-

Chemical Property:

• PSA: 46.53000
• LogP: 3.68720

Purity/Quality:

Analysis control,98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Kauran-20-oic acid,16,18-dihydroxy-, d-lactone, (4a)-

There total 28 articles about Kauran-20-oic acid,16,18-dihydroxy-, d-lactone, (4a)- 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: 73.0%

doianoterpene B → neotripterifordin (149249-32-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 40 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.7b02916

Reference yield:

{(R)-2-[(Z)-7-(3-Methoxy-phenyl)-4-vinyl-hept-4-enyl]-oxiranyl}-methanol (197369-40-7) → neotripterifordin (149249-32-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / n-Bu₄NI / tetrahydrofuran

2: 86 percent / TiCl₄ / CH₂Cl₂ / 0.17 h / -94 °C

3: 1.) Dess-Martin periodinane, 2.) H₂NNH₂, K₂CO₃, 3.) OsO₄, 4.) NaIO₄ / 1) CH₂Cl₂; 2) bis(ethylene glycol), 210 deg C; 3) t-BuOH-H₂O; 4) dioxane, H₂O

4: 98 percent / H₂, AcOH / Pd-C

5: 1.) Li, NH₃, 2.) HCl / 1) THF, t-BuOH; 2) MeOH

6: 72 percent / hexane / 0.5 h / -30 °C / Irradiation

7: 1.) O₃, NaHCO₃, MeOH, 2.) Me₂S, 3.) DIBAL-H / 1) -78 deg C; 2) 23 deg C, 15 h; 3) toluene, -78 deg C, 3 h

8: 94 percent / K₂CO₃ / methanol / 3 h / 23 °C

9: 1.) NaH, imidazole, 2.) CS₂, 3.) MeI, 4.) n-Bu₃SnH, AIBN / 1) THF, reflux, 3 h; 2) THF, 0.5 h; 3) THF, 0.5 h; 4) toluene, 110 deg C, 10 min

10: 1.) m-chloroperbenzoic acid, NaHCO₃, 2.) LiAlH₄, 3.) HCl, 4.) Dess-Martin periodinane / 1) CH₂Cl₂, 0 deg C, 30 min; 2) Et₂O, 23 deg C, 30 min; 3) THF, H₂O, 40 deg C, 2 h; 4) 23 deg C, 4 h

With 1H-imidazole; hydrogenchloride; methanol; carbon disulfide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); ammonia; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; ozone; acetic acid; 3-chloro-benzenecarboperoxoic acid; hydrazine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ja972549c

Reference yield:

(Z)-9-(3-Methoxy-phenyl)-2-methylene-6-vinyl-non-6-en-1-ol (197369-39-4) → neotripterifordin (149249-32-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, t-BUOOH, 4 Angstroem molecular sieves / CH₂Cl₂

2: 94 percent / n-Bu₄NI / tetrahydrofuran

3: 86 percent / TiCl₄ / CH₂Cl₂ / 0.17 h / -94 °C

4: 1.) Dess-Martin periodinane, 2.) H₂NNH₂, K₂CO₃, 3.) OsO₄, 4.) NaIO₄ / 1) CH₂Cl₂; 2) bis(ethylene glycol), 210 deg C; 3) t-BuOH-H₂O; 4) dioxane, H₂O

5: 98 percent / H₂, AcOH / Pd-C

6: 1.) Li, NH₃, 2.) HCl / 1) THF, t-BuOH; 2) MeOH

7: 72 percent / hexane / 0.5 h / -30 °C / Irradiation

8: 1.) O₃, NaHCO₃, MeOH, 2.) Me₂S, 3.) DIBAL-H / 1) -78 deg C; 2) 23 deg C, 15 h; 3) toluene, -78 deg C, 3 h

9: 94 percent / K₂CO₃ / methanol / 3 h / 23 °C

10: 1.) NaH, imidazole, 2.) CS₂, 3.) MeI, 4.) n-Bu₃SnH, AIBN / 1) THF, reflux, 3 h; 2) THF, 0.5 h; 3) THF, 0.5 h; 4) toluene, 110 deg C, 10 min

11: 1.) m-chloroperbenzoic acid, NaHCO₃, 2.) LiAlH₄, 3.) HCl, 4.) Dess-Martin periodinane / 1) CH₂Cl₂, 0 deg C, 30 min; 2) Et₂O, 23 deg C, 30 min; 3) THF, H₂O, 40 deg C, 2 h; 4) 23 deg C, 4 h

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; carbon disulfide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; ammonia; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; ozone; acetic acid; (-)-diethyl tartrate; 3-chloro-benzenecarboperoxoic acid; hydrazine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ja972549c

upstream raw materials:

C₂₁H₃₂O₂

{(R)-2-[(Z)-7-(3-Methoxy-phenyl)-4-vinyl-hept-4-enyl]-oxiranyl}-methanol

C₁₈H₂₆O₃

C₂₁H₃₀O₃

Refernces

• 1、 Corey,Liu. "Enantioselective total synthesis of the potent Anti-HIV agent neotripterifordin. Reassignment of stereochemistry at C(16)". . p. 9929 - 9930. Retrieved 2007/10/03.