(1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-one

Base Information

• Chemical Name: (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-one
• CAS No.: 122844-89-7
• Molecular Formula: C₂₆H₃₀O₃S
• Molecular Weight: 422.588

Synonyms:(1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-one

Chemical Property of (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-one

Chemical Property:

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Technology Process of (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-one

There total 10 articles about (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,4,6,11-tetraen-13-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%

tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane (122844-87-5,122844-88-6) → (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-13-one (122844-89-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)91209-8

Reference yield:

(phenylsulfanylmethyl)trimethylsilane (17873-08-4) → (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-13-one (122844-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1. BuLi / 1. THF, 0 deg C, 1 h; 2. THF a.) 0 deg C, 1 h, b.) r.t., 0.5 h

2: 80 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

With n-butyllithium; titanium tetrachloride; In dichloromethane;

DOI:10.1016/S0040-4020(01)91209-8

Reference yield:

m-anisaldehyde dimethyl acetal (59276-28-7) → (1S,9S,10S)-4,9-Dimethoxy-12,15,15-trimethyl-10-phenylsulfanyl-tricyclo[9.3.1.03,8]pentadeca-3(8),4,6,11-tetraen-13-one (122844-89-7)

Guidance literature:

Multi-step reaction with 8 steps

2: K₂CO₃ / methanol; H₂O / 7 h / Ambient temperature

3: PCC, NaOAc / CH₂Cl₂ / Ambient temperature

4: 1. LDA / 1. THF, -78 deg C, 1.5 h, 2. THF, a.) -78 deg C, 1.5 h, b.) 0 deg C, 1.5 h

5: t-BuOK / diethyl ether / 4 h / Ambient temperature

6: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7: 1. BuLi / 1. THF, 0 deg C, 1 h; 2. THF a.) 0 deg C, 1 h, b.) r.t., 0.5 h

8: 80 percent / TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

With n-butyllithium; potassium tert-butylate; sodium acetate; titanium tetrachloride; potassium carbonate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(01)91209-8

upstream raw materials:

tert-Butyl-{5-(2-dimethoxymethyl-6-methoxy-benzyl)-2,4,4-trimethyl-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-cyclohex-1-enyloxy}-dimethyl-silane

(phenylsulfanylmethyl)trimethylsilane

m-anisaldehyde dimethyl acetal

6-Bromo-4-hexen-3-yl acetate

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