1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl taxicine I

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Chemical Name:1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl taxicine I
CAS No.:182072-55-5
Molecular Formula:C₃₇H₅₆O₁₀SSi
Molecular Weight:720.997
Hs Code.:

Synonyms:1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl 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-5-O-mesyl 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-5-O-mesyl taxicine I

There total 7 articles about 1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl 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: 98.0%

: 124-63-0
methanesulfonyl chloride

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

: 182072-55-5
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl taxicine I

Guidance literature:: With pyridine; at 20 ℃; for 19.5h; ice cooling;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 182072-55-5
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl taxicine I

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 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 / 5: mesylation;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

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

: 182072-55-5
1,2-O-benzylidene-9,10-O-isopropylidene-4,20-dihydro-4α,20-dihydroxy-20-O-terbutyldimethylsilyl-5-O-mesyl taxicine I

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 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 / 5: mesylation;
DOI:10.1016/S0040-4020(97)00797-7