{(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid

Base Information

• Chemical Name: {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid
• CAS No.: 130399-27-8
• Molecular Formula: C₂₁H₂₆O₆S
• Molecular Weight: 406.5
• Mol file: 130399-27-8.mol

Synonyms:

Chemical Property of {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid

There total 5 articles about {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid 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:

(1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-3-oxo-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octane-5-acetaldehyde (130399-18-7) → {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid (130399-27-8)

Guidance literature:

With jones reagent; In acetone;

DOI:10.1248/cpb.38.1124

Reference yield:

tricyclo(3.3.0.02,8)octan-3-one (107344-32-1,116965-05-0) → {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid (130399-27-8)

Guidance literature:

Multi-step reaction with 5 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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; jones reagent; ozone; acetic acid; triethylamine; zinc; lithium diisopropyl amide; In 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) → {(1R,4aR,4bS)-3,3-Dimethyl-2-oxo-1-[2-(toluene-4-sulfonyloxy)-ethyl]-hexahydro-cyclopropa[cd]pentalen-4a-yl}-acetic acid (130399-27-8)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1248/cpb.38.1124

upstream raw materials:

(1RS,2SR,4SR,5SR,8SR)-7,7-dimethyl-3-oxo-4-<2-(p-tosyloxy)ethyl>tricyclo<3.3.0.0^2,8>octane-5-acetaldehyde

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