7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI

Base Information

• Chemical Name: 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI
• CAS No.: 196404-40-7
• Molecular Formula: C₃₂H₄₀O₉
• Molecular Weight: 568.664

Synonyms:7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI

Chemical Property of 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI

Chemical Property:

Purity/Quality:

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Technology Process of 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI

There total 9 articles about 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI 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: 48.0%

2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene-13-oxo baccatine IV (196404-39-4) → 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI (196404-40-7)

Guidance literature:

With tert.-butylhydroperoxide; 4 A molecular sieve; copper dichloride; In 2,2,4-trimethylpentane; toluene; for 15h;

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

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI (196404-40-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 7.67 h / 20 - 60 °C / ice cooling

2: 86 percent / aq. NaOH / tetrahydrofuran / 21.5 h / 20 °C / Heating

3: 59 percent / N-methylmorpholine N-oxide / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 62.5 h

4: 95 percent / imidazole / dimethylformamide / 2.25 h / 20 °C

5: 98 percent / pyridine / 19.5 h / 20 °C / ice cooling

6: 60 percent / tetrabutylammonium acetate / butan-2-one / 14.5 h / Heating

7: 44 percent / pyridine; DMAP / 21 h / 20 °C

8: 48 percent / CuCl₂; tert-BuOOH; 4 Angstroem molecular sieves / toluene; 2,2,4-trimethyl-pentane / 15 h

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium hydroxide; 4 A molecular sieve; tetrabutylammonium acetate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; copper dichloride; osmium(VIII) oxide; In tetrahydrofuran; 2,2,4-trimethylpentane; water; N,N-dimethyl-formamide; toluene; butanone; tert-butyl alcohol; 1: Cyclization / 2: Hydrolysis / 3: dihydroxylation / 4: silylation / 5: mesylation / 6: Cyclization / 7: Acetylation / 8: Oxidation;

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

Reference yield:

5-O-cinnamoyl-9,10-isopropylidenetaxicine I (14550-93-7) → 7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene-13-oxo baccatine VI (196404-40-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 7.67 h / 20 - 60 °C / ice cooling

2: 86 percent / aq. NaOH / tetrahydrofuran / 21.5 h / 20 °C / Heating

3: 59 percent / N-methylmorpholine N-oxide / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 62.5 h

4: 95 percent / imidazole / dimethylformamide / 2.25 h / 20 °C

5: 98 percent / pyridine / 19.5 h / 20 °C / ice cooling

6: 60 percent / tetrabutylammonium acetate / butan-2-one / 14.5 h / Heating

7: 44 percent / pyridine; DMAP / 21 h / 20 °C

8: 48 percent / CuCl₂; tert-BuOOH; 4 Angstroem molecular sieves / toluene; 2,2,4-trimethyl-pentane / 15 h

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium hydroxide; 4 A molecular sieve; tetrabutylammonium acetate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; copper dichloride; osmium(VIII) oxide; In tetrahydrofuran; 2,2,4-trimethylpentane; water; N,N-dimethyl-formamide; toluene; butanone; tert-butyl alcohol; 1: Cyclization / 2: Hydrolysis / 3: dihydroxylation / 4: silylation / 5: mesylation / 6: Cyclization / 7: Acetylation / 8: Oxidation;

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

upstream raw materials:

2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene-13-oxo baccatine IV

benzaldehyde dimethyl acetal

5-O-cinnamoyl-9,10-isopropylidenetaxicine I

1,2-O-benzylidene-9,10-O-isopropylidene taxicine I

Downstream raw materials:

7-desacetoxy-9,10,13-tridesacetyl-9,10-O-isopropylidene baccatine VI

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