7-deshydroxy-13-deshydro baccatine III

Base Information

• Chemical Name: 7-deshydroxy-13-deshydro baccatine III
• CAS No.: 214192-74-2
• Molecular Formula: C₃₁H₃₆O₁₀
• Molecular Weight: 568.621
• Mol file: 214192-74-2.mol

Synonyms:7-deshydroxy-13-deshydro baccatine III

Chemical Property of 7-deshydroxy-13-deshydro baccatine III

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-deshydroxy-13-deshydro baccatine III

There total 31 articles about 7-deshydroxy-13-deshydro baccatine III 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: 54.0%

2-debenzoyl-1,2-O-benzylidene-7-deshydroxy-13-deshydro baccatine III → 7-deshydroxy-13-deshydro baccatine III (214192-74-2)

Guidance literature:

With tert.-butylhydroperoxide; 4 A molecular sieve; copper dichloride; In 2,2,4-trimethylpentane; toluene; for 24h;

DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

9-O-Acetyl-5-O-cinnamoyltaxicine I (146257-44-5) → 7-deshydroxy-13-deshydro baccatine III (214192-74-2)

Guidance literature:

Multi-step reaction with 13 steps

1: KOAc / methanol / 12 h / 20 °C

2: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: H₂O; imidazole / diethyl ether / 0.17 h / 20 °C

4: 80 percent / Dess-Martin periodinane; TFA / CH₂Cl₂ / 12 h / 20 °C

5: 100 percent / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 20 °C

6: 80 percent / KOAc / 0.37 h / Heating

7: 83 percent / DMAP; NEt₃ / CH₂Cl₂ / 24 h / 20 °C

8: 97 percent / pyridine / 24 h / 20 °C

9: 80 percent / HF / acetonitrile / 6.5 h / 20 °C

10: 82 percent / diisopropylamine / toluene / 39 h / Heating

11: 66 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

12: tetrahydrofuran / 0.5 h / -78 °C

13: DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen fluoride; water; potassium acetate; Dess-Martin periodane; triethylamine; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1: Isomerization / 2: Cyclization / 3: Hydrolysis / 4: Oxidation / 5: Oxidation / 6: Methanolysis / 7: Etherification / 8: Mesylation / 9: Desilylation / 10: Cyclization / 11: Acetylation / 12: Ring cleavage / 13: Acetylation;

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 7-deshydroxy-13-deshydro baccatine III (214192-74-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 7.67 h / 20 - 60 °C / ice cooling

2.1: 86 percent / aq. NaOH / tetrahydrofuran / 21.5 h / 20 °C / Heating

3.1: 59 percent / N-methylmorpholine N-oxide / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 62.5 h

4.1: 95 percent / imidazole / dimethylformamide / 2.25 h / 20 °C

5.1: 98 percent / pyridine / 19.5 h / 20 °C / ice cooling

6.1: 84 percent / p-toluenesulfonic acid / acetonitrile; methanol; H₂O / 15 h / 20 °C

7.1: 77 percent / imidazole / dimethylformamide / 4 h / 20 °C

8.1: p-toluenesulfonic acid / tetrahydrofuran / 0.25 h / 58 °C

9.1: p-toluenesulfonic acid / tetrahydrofuran / 0.75 h / 20 - 58 °C

9.2: 224.6 mg / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / acetonitrile / 1 h / 20 °C

10.1: 100 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 20 °C

11.1: 49 percent / tetrabutylammonium acetate / butan-2-one / 13.5 h / 70 °C

12.1: 48 percent / pyridine; DMAP / 15.5 h / 20 °C

13.1: 54 percent / CuCl₂; tert-BuOOH; 4 Angstroem molecular sieves / toluene; 2,2,4-trimethyl-pentane / 24 h

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammonium acetate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; copper dichloride; osmium(VIII) oxide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; water; N,N-dimethyl-formamide; toluene; acetonitrile; butanone; tert-butyl alcohol; 1.1: Cyclization / 2.1: Hydrolysis / 3.1: dihydroxylation / 4.1: silylation / 5.1: mesylation / 6.1: Hydrolysis / 7.1: silylation / 8.1: Cyclization / 9.1: Ring cleavage / 9.2: Oxidation / 10.1: desilylation / 11.1: Cyclization / 12.1: Acetylation / 13.1: Oxidation;

DOI:10.1016/S0040-4020(97)00797-7

upstream raw materials:

acetic anhydride

phenyllithium

C₂₅H₃₀O₁₀

9-O-Acetyl-5-O-cinnamoyltaxicine I

Downstream raw materials:

7-deoxypaclitaxel

7-deshydroxy baccatine III