(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester

Base Information

• Chemical Name: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester
• CAS No.: 82799-07-3
• Molecular Formula: C₃₀H₃₇F₃O₄
• Molecular Weight: 518.617
• Mol file: 82799-07-3.mol

Synonyms:(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester

Chemical Property of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester

There total 4 articles about (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-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: 100.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (3aS,4aR,8S,8aS,10aR)-8-Hydroxy-1-isopropylidene-3a,8a-dimethyl-5-methylene-dodecahydro-benzo[f]azulen-2-one (82799-00-6) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester (82799-07-3)

Guidance literature:

With pyridine; In tetrachloromethane; Ambient temperature; overnight;

DOI:10.1021/jo00142a024

Reference yield:

(S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester (82799-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride, sodium chloride / 60 h / Heating

2: 100 percent / pyridine / CCl₄ / Ambient temperature; overnight

With pyridine; thionyl chloride; sodium chloride; In tetrachloromethane;

DOI:10.1021/jo00142a024

Reference yield:

13-keto-1(S),11(R)-dolabella-3(E),7(E),12(18)-triene (82798-98-9) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,4aR,8S,8aS,10aR)-1-isopropylidene-3a,8a-dimethyl-5-methylene-2-oxo-tetradecahydro-benzo[f]azulen-8-yl ester (82799-07-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature; Na₂HPO₄-buffer

2: 17 percent / BF₃-etherate / diethyl ether / 0.25 h / 0 °C

3: 100 percent / pyridine / CCl₄ / Ambient temperature; overnight

With pyridine; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In tetrachloromethane; diethyl ether; dichloromethane;

DOI:10.1021/jo00142a024

upstream raw materials:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

(3aS,4aR,8S,8aS,10aR)-8-Hydroxy-1-isopropylidene-3a,8a-dimethyl-5-methylene-dodecahydro-benzo[f]azulen-2-one

(S)-Mosher acid

13-keto-1(S),11(R)-dolabella-3(E),7(E),12⁽¹⁸⁾-triene