(1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl ester
• CAS No.: 138060-44-3
• Molecular Formula: C₂₁H₂₃NO₇S
• Molecular Weight: 433.482

Synonyms:(1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl ester

Chemical Property of (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl ester

There total 5 articles about (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl 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: 78.0%

(1S,7R,9R)-9-(3-Hydroxy-propyl)-3-oxo-2-oxa-8-aza-tricyclo[5.2.2.01,5]undeca-4,10-diene-8-carboxylic acid methyl ester (138060-43-2) + p-toluenesulfonyl chloride (98-59-9) → (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.01,5]undeca-4,10-diene-8-carboxylic acid methyl ester (138060-44-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 5h;

DOI:10.1016/S0040-4020(01)88027-3

Reference yield:

3-HYDROXYPYRIDINE (109-00-2) → (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.01,5]undeca-4,10-diene-8-carboxylic acid methyl ester (138060-44-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.17 h

2: 81 percent / CH₂Cl₂ / 3 h / 25 °C

3: 45 percent / KF*2H₂O / methanol; acetic acid / 17 h

4: 1.) 2-methyl-2-butene, BH₃*THF; 2.) 30percent aq. H₂O₂, 2M NaOH / 1.) a.) 0 deg C, 1 h; b.) -23 deg C, 2.5 h; 2.) 0.5 h

5: 78 percent / Et₃N, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 5 h

With dmap; potassium fluoride; sodium hydroxide; borane-THF; 2-methyl-but-2-ene; dihydrogen peroxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(01)88027-3

Reference yield:

2-Allyl-3-(4-trimethylsilanyl-but-2-ynoyloxy)-2H-pyridine-1-carboxylic acid methyl ester (138060-41-0) → (1R,7S,9S)-3-Oxo-9-[3-(toluene-4-sulfonyloxy)-propyl]-2-oxa-8-aza-tricyclo[5.2.2.01,5]undeca-4,10-diene-8-carboxylic acid methyl ester (138060-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / KF*2H₂O / methanol; acetic acid / 17 h

2: 1.) 2-methyl-2-butene, BH₃*THF; 2.) 30percent aq. H₂O₂, 2M NaOH / 1.) a.) 0 deg C, 1 h; b.) -23 deg C, 2.5 h; 2.) 0.5 h

3: 78 percent / Et₃N, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 5 h

With dmap; potassium fluoride; sodium hydroxide; borane-THF; 2-methyl-but-2-ene; dihydrogen peroxide; triethylamine; In methanol; dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(01)88027-3

upstream raw materials:

(1S,7R,9R)-9-(3-Hydroxy-propyl)-3-oxo-2-oxa-8-aza-tricyclo[5.2.2.0^1,5]undeca-4,10-diene-8-carboxylic acid methyl ester

p-toluenesulfonyl chloride

3-HYDROXYPYRIDINE

4-Trimethylsilanyl-but-2-ynoic acid pyridin-3-yl ester

Downstream raw materials:

(+/-)-norsecurinine

C₂₄H₂₂F₅NO₆S

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