Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

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Chemical Name:Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester
CAS No.:175979-30-3
Molecular Formula:C₂₂H₃₀O₅Si
Molecular Weight:402.563
Hs Code.:

Synonyms:Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

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Chemical Property of Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

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Technology Process of Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

There total 9 articles about Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester 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:

: 130021-74-8
(1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

: 175979-30-3
Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 - 25 °C

2: 97 percent / imidazole, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

3: 75 percent / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile / 0.05 h / 0 °C

4: 97 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

5: 89 percent / SO₂Cl₂ / pyridine; CH₂Cl₂ / 2.5 h / 0 °C

6: 80 percent / TFA / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

7: 1.) 1,1'-thiocarbonyldiimidazole, 2.) P(OMe)3 / 1.) TolH, reflux, 24 h, 2.) reflux, 24 h

With 1H-imidazole; 2,3,5-trimethyl-pyridine; dmap; ruthenium trichloride; sodium periodate; sulfuryl dichloride; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo970907o

Reference yield:

: 203317-81-1
(1R,2R,3S)-5-(benzoyloxymethyl)-1,2-O-cyclohexylidene-4-cyclohexene-1,2,3-triol

: 175979-30-3
Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / imidazole, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

2: 75 percent / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile / 0.05 h / 0 °C

3: 97 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

4: 89 percent / SO₂Cl₂ / pyridine; CH₂Cl₂ / 2.5 h / 0 °C

5: 80 percent / TFA / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

6: 1.) 1,1'-thiocarbonyldiimidazole, 2.) P(OMe)3 / 1.) TolH, reflux, 24 h, 2.) reflux, 24 h

With 1H-imidazole; dmap; ruthenium trichloride; sodium periodate; sulfuryl dichloride; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo970907o

Reference yield:

: 175979-28-9
(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

: 175979-30-3
Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / SO₂Cl₂ / pyridine; CH₂Cl₂ / 2.5 h / 0 °C

2: 80 percent / TFA / H₂O; CH₂Cl₂ / 6 h / Ambient temperature

3: 1.) 1,1'-thiocarbonyldiimidazole, 2.) P(OMe)3 / 1.) TolH, reflux, 24 h, 2.) reflux, 24 h

With sulfuryl dichloride; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; dichloromethane; water;
DOI:10.1021/jo970907o