(1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid

Base Information

• Chemical Name: (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid
• CAS No.: 164414-36-2
• Molecular Formula: C₁₇H₃₂O₄Si
• Molecular Weight: 328.524

Synonyms:(1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid

Chemical Property of (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid

There total 2 articles about (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic 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: 91.0%

(1R,2R,3R)-(-)-3-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid methyl ester → (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid (164414-36-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 15h; Ambient temperature;

DOI:10.1016/0040-4039(95)00475-R

Reference yield: 91.0%

[(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethyl-cyclohex-(E)-ylidene]-(1-phenyl-ethyl)-amine → (1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid (164414-36-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1055/s-1997-1492

Reference yield:

(1R,2R,3R)-(-)-<3-(tert-butyldimethylsiloxy)-1,2-dimethyl-6-oxocyclohexyl>propionic acid (164414-36-2) → Petasin (26577-85-5)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene / 5 h / 80 °C

2: ethanol / 15 h / Heating

3: 1.) HMDS, 3.) ZnCl₂

4: 94 percent / 50percent aq. HF / acetonitrile / 2 h / Ambient temperature

5: Et₃N / toluene / 24 h / 80 °C

6: 69 percent / (CF₃SO₂)O, i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

With trifluoromethylsulfonic anhydride; hydrogen fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1055/s-1997-1492

Downstream raw materials:

Petasin

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