Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester
• CAS No.: 175979-33-6
• Molecular Formula: C₂₂H₃₀O₇Si
• Molecular Weight: 434.562

Synonyms:Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Chemical Property of Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

There total 12 articles about Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl 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: 100.0%

Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester (175979-31-4) → Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-ylmethyl ester (175979-33-6)

Guidance literature:

With CoTPP; In chloroform; at 0 ℃; for 3h;

DOI:10.1021/jo970907o

Reference yield:

(1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol (130021-74-8) → Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-ylmethyl ester (175979-33-6)

Guidance literature:

Multi-step reaction with 9 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

8: 78.5 percent / O₂, TPP / CCl₄ / 7 h / Irradiation

9: 100 percent / CoTPP / CHCl₃ / 3 h / 0 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; dmap; ruthenium trichloride; sodium periodate; sulfuryl dichloride; oxygen; thiamine diphosphate; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; tetrachloromethane; dichloromethane; chloroform; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo970907o

Reference yield:

Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester (175979-30-3) → Benzoic acid (1R,2R,4R,5S,6R,7S)-5-acetoxy-6-(tert-butyl-dimethyl-silanyloxy)-3,8-dioxa-tricyclo[5.1.0.02,4]oct-4-ylmethyl ester (175979-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.5 percent / O₂, TPP / CCl₄ / 7 h / Irradiation

2: 100 percent / CoTPP / CHCl₃ / 3 h / 0 °C

With oxygen; thiamine diphosphate; In tetrachloromethane; chloroform;

DOI:10.1021/jo970907o

upstream raw materials:

Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester

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

(1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

benzoyl chloride

Downstream raw materials:

4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octane-5,6-diol 5-acetate

(+)-boesenboxide

(+)-crotepoxide

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