1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

Base Information

Chemical Name:1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel
CAS No.:181797-15-9
Molecular Formula:C₅₅H₆₉NO₁₃
Molecular Weight:952.152
Hs Code.:

Synonyms:1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

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Chemical Property of 1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

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Technology Process of 1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

There total 11 articles about 1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-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: 80.0%

: (4S,5R)-5-(1-Ethoxy-ethoxy)-2,4-diphenyl-4,5-dihydro-[1,3]oxazin-6-one

: 181797-14-8
1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-9(R)-dihydrobaccatin III

: 181797-15-9
1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

Guidance literature:: With dmap; In pyridine; toluene; for 12h; Ambient temperature;
DOI:10.1021/jo960438a

Reference yield:

: 181797-12-6
C₂₈H₄₂O₈

: 181797-15-9
1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / Et₃N, DMAP / ethyl acetate / 24 h / Ambient temperature

2: 21 percent / BH₃*THF / tetrahydrofuran / 3 h / Ambient temperature

3: 80 percent / DMAP / pyridine; toluene / 12 h / Ambient temperature

With dmap; borane-THF; triethylamine; In tetrahydrofuran; pyridine; ethyl acetate; toluene;
DOI:10.1021/jo960438a

Reference yield:

: 14550-93-7
5-O-cinnamoyl-9,10-isopropylidenetaxicine I

: 181797-15-9
1-benzoyl-2-debenzoyl-2-(tetrahydropyran-2-yl)-4-deacetyl-7-deoxy-10-deacetyl-9,10-O-(propane-2,2-diyl)-2'-ethoxyethyl-9(R)-dihydropaclitaxel

Guidance literature:: Multi-step reaction with 11 steps

1: 82 percent / 9,10-O-(propane-2,2-diyl)-5α-cinnamoyltaxicin-II, p-TsOH / CH2Cl2 / 24 h / Ambient temperature

2: 95 percent / aq. NaOH (20 N) / tetrahydrofuran / 48 h / Heating

3: 75 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: 89 percent / pyridine / 20 h / Ambient temperature

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

7: 77 percent / tetrabutylammonium acetate / butan-2-one / 17 h / Heating

8: 89 percent / HOAc, H₂O / tetrahydrofuran / 24 h / Ambient temperature

9: 96 percent / Et₃N, DMAP / ethyl acetate / 24 h / Ambient temperature

10: 21 percent / BH₃*THF / tetrahydrofuran / 3 h / Ambient temperature

11: 80 percent / DMAP / pyridine; toluene / 12 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; osmium(VIII) oxide; borane-THF; 9,10-O-(propane-2,2-diyl)-5α-cinnamoyltaxicin-II; tetrabutyl ammonium fluoride; water; tetrabutylammonium acetate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; toluene; butanone; tert-butyl alcohol;
DOI:10.1021/jo960438a