Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

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Chemical Name:Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester
CAS No.:175979-29-0
Molecular Formula:C₂₂H₃₂O₇Si
Molecular Weight:436.577
Hs Code.:

Synonyms:Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

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Chemical Property of Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

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Technology Process of Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

There total 8 articles about Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl 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: 80.0%

: 203317-83-3
(1R,2R,3S,4R)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidene-5-cyclohexene-1,2,3,4-tetrol

: 175979-29-0
Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; Ambient temperature;
DOI:10.1016/0957-4166(96)00004-3

Reference yield:

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

: 175979-29-0
Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; 2,3,5-trimethyl-pyridine; dmap; ruthenium trichloride; sodium periodate; sulfuryl dichloride; trifluoroacetic acid; 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

: 175979-29-0
Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester

Guidance literature:: Multi-step reaction with 5 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

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