Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester

Base Information

• Chemical Name: Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester
• CAS No.: 129064-48-8
• Molecular Formula: C₃₀H₃₄NO₅P
• Molecular Weight: 519.577

Synonyms:Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester

Chemical Property of Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester

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Technology Process of Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester

There total 4 articles about Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl 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: 61.0%

(1R,2S,6R,7S)-1,10,10-Trimethyl-4-vinyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene (129064-51-3) + diphenyl 1,3-cyclopentadiene-2-yl phosphate (129064-38-6) → Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester (129064-48-8)

Guidance literature:

With trifluoroacetic anhydride; calcium carbonate; In dichloromethane; at -78 ℃; for 1.5h;

Reference yield:

cyclopent-2-enone (930-30-3) → Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester (129064-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, HMPA, -78 deg C, 5 min, 2.) -78 deg C, 15 min

2: 61 percent / trifluoroacetic anhydride, CaCO₃ / CH₂Cl₂ / 1.5 h / -78 °C

With trifluoroacetic anhydride; calcium carbonate; lithium diisopropyl amide; In dichloromethane;

Reference yield:

(1R,2S,6R,7S)-4-(2-Isopropoxy-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-ene (129064-50-2) → Phosphoric acid diphenyl ester (1S,4S,5S)-5-((1R,2S,6R,7S)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.02,6]dec-4-en-4-yl)-bicyclo[2.2.1]hept-2-en-2-yl ester (129064-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / t-BuOK, 18-crown-6 ether, phenothiazine / tetrahydrofuran / 0.25 h / 0 °C

2: 61 percent / trifluoroacetic anhydride, CaCO₃ / CH₂Cl₂ / 1.5 h / -78 °C

With 10H-phenothiazine; 18-crown-6 ether; potassium tert-butylate; trifluoroacetic anhydride; calcium carbonate; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(1R,2S,6R,7S)-1,10,10-Trimethyl-4-vinyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

diphenyl 1,3-cyclopentadiene-2-yl phosphate

cyclopent-2-enone

(1R,2S,6R,7S)-4-(2-Isopropoxy-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene

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