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

Base Information

Chemical Name:1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl taxicine I
CAS No.:196404-48-5
Molecular Formula:C₃₀H₃₈O₁₁S
Molecular Weight:606.691
Hs Code.:

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

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Chemical Property of 1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl taxicine I

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Technology Process of 1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl taxicine I

There total 10 articles about 1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl 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: 100.0%

: 196404-46-3
1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl-20-O-terbutyldimethylsilyl taxicine I

: 196404-48-5
1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl taxicine I

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 196404-48-5
1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl taxicine I

Guidance literature:: Multi-step reaction with 10 steps

1.1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 7.67 h / 20 - 60 °C / ice cooling

2.1: 86 percent / aq. NaOH / tetrahydrofuran / 21.5 h / 20 °C / Heating

3.1: 59 percent / N-methylmorpholine N-oxide / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 62.5 h

4.1: 95 percent / imidazole / dimethylformamide / 2.25 h / 20 °C

5.1: 98 percent / pyridine / 19.5 h / 20 °C / ice cooling

6.1: 84 percent / p-toluenesulfonic acid / acetonitrile; methanol; H₂O / 15 h / 20 °C

7.1: 77 percent / imidazole / dimethylformamide / 4 h / 20 °C

8.1: p-toluenesulfonic acid / tetrahydrofuran / 0.25 h / 58 °C

9.1: p-toluenesulfonic acid / tetrahydrofuran / 0.75 h / 20 - 58 °C

9.2: 224.6 mg / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / acetonitrile / 1 h / 20 °C

10.1: 100 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Cyclization / 2.1: Hydrolysis / 3.1: dihydroxylation / 4.1: silylation / 5.1: mesylation / 6.1: Hydrolysis / 7.1: silylation / 8.1: Cyclization / 9.1: Ring cleavage / 9.2: Oxidation / 10.1: desilylation;
DOI:10.1016/S0040-4020(97)00797-7

Reference yield:

: 1,2-O-benzylidene-9,10-isopropylidene-5-O-cinnamoyl taxicine I

: 196404-48-5
1,2-O-benzylidene-4,20-dihydro-4α,20-dihydroxy-5-O-mesyl-9-deshydro-10-acetyl taxicine I

Guidance literature:: Multi-step reaction with 9 steps

1.1: 86 percent / aq. NaOH / tetrahydrofuran / 21.5 h / 20 °C / Heating

2.1: 59 percent / N-methylmorpholine N-oxide / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 62.5 h

3.1: 95 percent / imidazole / dimethylformamide / 2.25 h / 20 °C

4.1: 98 percent / pyridine / 19.5 h / 20 °C / ice cooling

5.1: 84 percent / p-toluenesulfonic acid / acetonitrile; methanol; H₂O / 15 h / 20 °C

6.1: 77 percent / imidazole / dimethylformamide / 4 h / 20 °C

7.1: p-toluenesulfonic acid / tetrahydrofuran / 0.25 h / 58 °C

8.1: p-toluenesulfonic acid / tetrahydrofuran / 0.75 h / 20 - 58 °C

8.2: 224.6 mg / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / acetonitrile / 1 h / 20 °C

9.1: 100 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: dihydroxylation / 3.1: silylation / 4.1: mesylation / 5.1: Hydrolysis / 6.1: silylation / 7.1: Cyclization / 8.1: Ring cleavage / 8.2: Oxidation / 9.1: desilylation;
DOI:10.1016/S0040-4020(97)00797-7