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

Base Information

Chemical Name:Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester
CAS No.:176198-54-2
Molecular Formula:C₂₂H₃₀O₇Si
Molecular Weight:434.562
Hs Code.:

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

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

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

There total 10 articles about Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-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: 78.5%

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

: 175979-31-4
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

: 176198-54-2
Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester

Guidance literature:: With oxygen; thiamine diphosphate; In tetrachloromethane; for 7h; Irradiation;
DOI:10.1021/jo970907o

Reference yield:

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

: 176198-54-2
Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 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: 1.5 percent / O₂, TPP / CCl₄ / 7 h / Irradiation

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; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo970907o

Reference yield:

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

: 176198-54-2
Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: 1.5 percent / O₂, TPP / CCl₄ / 7 h / Irradiation

With oxygen; thiamine diphosphate; 1,1'-Thiocarbonyldiimidazole; phosphorous acid trimethyl ester; In tetrachloromethane;
DOI:10.1021/jo970907o