(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

Base Information

• Chemical Name: (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
• CAS No.: 130399-17-6
• Molecular Formula: C₂₂H₂₈O₄S
• Molecular Weight: 388.528
• Mol file: 130399-17-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 80.0%

(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) + p-toluenesulfonyl chloride (98-59-9) → (1RS,2SR,4SR,5RS,8SR)-7,7-dimethyl-5-(2-propen-1-yl)-4-<(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octan-3-one (130399-17-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1248/cpb.38.1124

Reference yield:

tricyclo(3.3.0.02,8)octan-3-one (107344-32-1,116965-05-0) → (1RS,2SR,4SR,5RS,8SR)-7,7-dimethyl-5-(2-propen-1-yl)-4-<(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octan-3-one (130399-17-6)

Guidance literature:

Multi-step reaction with 3 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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; triethylamine; lithium diisopropyl amide; In 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) → (1RS,2SR,4SR,5RS,8SR)-7,7-dimethyl-5-(2-propen-1-yl)-4-<(p-tosyloxy)ethyl>tricyclo<3.3.0.02,8>octan-3-one (130399-17-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With hydrogenchloride; dmap; triethylamine; In dichloromethane; acetone;

DOI:10.1248/cpb.38.1124

upstream raw materials:

(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

p-toluenesulfonyl chloride

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

Downstream raw materials:

(1RS,2SR,4SR,8RS,11SR)-10,10-dimethyl-7-<(p-tosyloxy)methyl>tetracyclo<6.3.0.0^2,11.0^4,8>undecan-3-one

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

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

(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