methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octane-5-acetate

Base Information

• Chemical Name: methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octane-5-acetate
• CAS No.: 130399-19-8
• Molecular Formula: C₂₂H₂₈O₆S
• Molecular Weight: 420.527
• Mol file: 130399-19-8.mol

Synonyms:

Chemical Property of methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octane-5-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octane-5-acetate

There total 5 articles about methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octane-5-acetate 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:

tricyclo(3.3.0.02,8)octan-3-one (107344-32-1,116965-05-0) → methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octane-5-acetate (130399-19-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) LDA, 2) HMPA / 1) THF, -78 deg C, 20 min, 2) -78 deg C, 15 min, 3) THF, -78 deg C to RT

2: 100 percent / 1N HCl / acetone / 12 h / Ambient temperature

3: 80 percent / NEt₃, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

4: 1) O₃, 2) Zn, HOAc / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 2h

5: Jones reagent / acetone

6: diethyl ether / 0.5 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; jones reagent; ozone; acetic acid; triethylamine; zinc; lithium diisopropyl amide; In diethyl ether; dichloromethane; acetone;

DOI:10.1248/cpb.38.1124

Reference yield:

(1RS,2SR,4SR,5RS,8SR)-4-(2-hydroxyethyl)-7,7-dimethyl-5-(2-propen-1-yl)tricyclo<3.3.0.02,8>octan-3-one (130399-16-5) → methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octane-5-acetate (130399-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / NEt₃, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

2: 1) O₃, 2) Zn, HOAc / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 2h

3: Jones reagent / acetone

4: diethyl ether / 0.5 h

With dmap; jones reagent; ozone; acetic acid; triethylamine; zinc; In diethyl ether; dichloromethane; acetone;

DOI:10.1248/cpb.38.1124

Reference yield:

(1RS,2SR,4SR,5RS,8SR)-7,7-dimethyl-5-(2-propen-1-yl)-4-<2-<(tetrahydropyran-2-yl)oxy>ethyl>tricyclo<3.3.0.02,8>octan-3-one (130399-15-4) → methyl (1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octane-5-acetate (130399-19-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 1N HCl / acetone / 12 h / Ambient temperature

2: 80 percent / NEt₃, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

3: 1) O₃, 2) Zn, HOAc / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 2h

4: Jones reagent / acetone

5: diethyl ether / 0.5 h

With hydrogenchloride; dmap; jones reagent; ozone; acetic acid; triethylamine; zinc; In diethyl ether; dichloromethane; acetone;

DOI:10.1248/cpb.38.1124

upstream raw materials:

tricyclo(3.3.0.0^2,8)octan-3-one

(1RS,2SR,4SR,5RS,8SR)-4-(2-hydroxyethyl)-7,7-dimethyl-5-(2-propen-1-yl)tricyclo<3.3.0.0^2,8>octan-3-one

(1RS,2SR,4SR,5RS,8SR)-7,7-dimethyl-5-(2-propen-1-yl)-4-<2-<(tetrahydropyran-2-yl)oxy>ethyl>tricyclo<3.3.0.0^2,8>octan-3-one

(1RS,2SR,4SR,5RS,8SR)-7,7-dimethyl-5-(2-propen-1-yl)-4-<(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octan-3-one