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

Base Information

Chemical Name:2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV
CAS No.:196404-36-1
Molecular Formula:C₃₂H₄₂O₈
Molecular Weight:554.681
Hs Code.:

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

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Chemical Property of 2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV

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Technology Process of 2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV

There total 9 articles about 2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV 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: 63.0%

: 196404-39-4
2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene-13-oxo baccatine IV

: 196404-36-1
2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 196404-36-1
2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV

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: 63 percent / DIBALH / toluene / 0.33 h / -78 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; tetrabutylammonium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; 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: Reduction;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

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

: 196404-36-1
2,9,10,13-tetradesacetyl-1,2-O-benzylidene-7-desacetoxy-9,10-O-isopropylidene baccatine IV

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: 63 percent / DIBALH / toluene / 0.33 h / -78 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; tetrabutylammonium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; 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: Reduction;
DOI:10.1016/S0040-4020(97)00797-7