2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel

Base Information

• Chemical Name: 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel
• CAS No.: 181797-18-2
• Molecular Formula: C₄₆H₅₃NO₁₀
• Molecular Weight: 779.928

Synonyms:2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel

Chemical Property of 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel

Chemical Property:

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Technology Process of 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel

There total 11 articles about 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel 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%

2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-(ethoxyethyl)-9(R)-dihydropaclitaxel → 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel (181797-18-2)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo960438a

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel (181797-18-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / 9,10-O-(propane-2,2-diyl)-5α-cinnamoyltaxicin-II, p-TsOH / CH2Cl2 / 24 h / Ambient temperature

2: 76 percent / aq. NaOH (20 N) / tetrahydrofuran / 48 h / Heating

3: 55 percent / N-methylmorpholine N-oxide monohydrate, OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 h

4: 1.) imidazole / 1) DMF, 15 min; 2) DMF, 3 h

5: 83 percent / pyridine / 20 h / Ambient temperature

6: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

7: 64 percent / tetrabutylammonium acetate / butan-2-one / 17 h / Heating

8: 46 percent / DIBALH / CH₂Cl₂ / 3 h / 0 °C

9: 70 percent / DMAP / pyridine; toluene / 12 h / Ambient temperature

10: 73 percent / HOAc, H₂O / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; 9,10-O-(propane-2,2-diyl)-5α-cinnamoyltaxicin-II; tetrabutyl ammonium fluoride; water; tetrabutylammonium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; pyridine; dichloromethane; water; toluene; butanone; tert-butyl alcohol;

DOI:10.1021/jo960438a

Reference yield:

5-O-cinnamoyl-9,10-isopropylidenetaxicine I (14550-93-7) → 2-debenzoyl-1,2-O-benzylidene-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydropaclitaxel (181797-18-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / 9,10-O-(propane-2,2-diyl)-5α-cinnamoyltaxicin-II, p-TsOH / CH2Cl2 / 24 h / Ambient temperature

2: 76 percent / aq. NaOH (20 N) / tetrahydrofuran / 48 h / Heating

3: 55 percent / N-methylmorpholine N-oxide monohydrate, OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 h

4: 1.) imidazole / 1) DMF, 15 min; 2) DMF, 3 h

5: 83 percent / pyridine / 20 h / Ambient temperature

6: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

7: 64 percent / tetrabutylammonium acetate / butan-2-one / 17 h / Heating

8: 46 percent / DIBALH / CH₂Cl₂ / 3 h / 0 °C

9: 70 percent / DMAP / pyridine; toluene / 12 h / Ambient temperature

10: 73 percent / HOAc, H₂O / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; 9,10-O-(propane-2,2-diyl)-5α-cinnamoyltaxicin-II; tetrabutyl ammonium fluoride; water; tetrabutylammonium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; pyridine; dichloromethane; water; toluene; butanone; tert-butyl alcohol;

DOI:10.1021/jo960438a

upstream raw materials:

benzaldehyde dimethyl acetal

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

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