1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

Base Information

Chemical Name:1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I
CAS No.:182208-88-4
Molecular Formula:C₃₆H₅₄O₈Si
Molecular Weight:642.905
Hs Code.:

Synonyms:1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

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Chemical Property of 1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

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Technology Process of 1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

There total 5 articles about 1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I 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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 182072-54-4
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy taxicine I

: 182208-88-4
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2.25h;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 182208-88-4
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; sodium hydroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Cyclization / 2: Hydrolysis / 3: dihydroxylation / 4: silylation;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

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

: 182208-88-4
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl taxicine I

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; sodium hydroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Cyclization / 2: Hydrolysis / 3: dihydroxylation / 4: silylation;
DOI:10.1016/S0040-4020(97)00797-7