(+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether
• CAS No.: 136954-91-1
• Molecular Formula: C₂₇H₄₂O₃Si
• Molecular Weight: 442.714
• Mol file: 136954-91-1.mol

Synonyms:

Chemical Property of (+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether

There total 7 articles about (+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether 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: 60.0%

(+/-)-9-normethyl-9-(1,3-dithianyl)-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether (136954-90-0) → (+/-)-11-oxo-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether (136954-91-1,138285-36-6)

Guidance literature:

With potassium carbonate; methyl iodide; In water; N,N-dimethyl-formamide; for 5h; Ambient temperature;

DOI:10.1021/jo00024a031

Reference yield: 52.0%

11-oxo-6a,10a-trans-Δ9-THC (52663-85-1,67145-57-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (+/-)-11-oxo-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether (136954-91-1,138285-36-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1055/s-1991-26590

Reference yield:

(+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone (67119-85-1) → (+/-)-11-oxo-Δ9-tetrahydrocannabiol tert-butyldimethylsilyl ether (136954-91-1,138285-36-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) n-BuLi / 1) THF, hexane, -30 deg C, 1.5 h, 2) THF, room temperature, 0.5 h

2: 19 percent / p-TosOH*H₂O / benzene / 0.25 h / 85 - 90 °C

3: 61 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

4: 60 percent / CH₃I, K₂CO₃ / dimethylformamide; H₂O / 5 h / Ambient temperature

With 1H-imidazole; n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; methyl iodide; In water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00024a031

upstream raw materials:

(+/-)-9-normethyl-9-(1,3-dithianyl)-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether

11-oxo-6a,10a-trans-Δ⁹-THC

tert-butyldimethylsilyl chloride

(+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone

Downstream raw materials:

(+/-)-11-Nor-9-carboxy-Δ⁹-tetrahydrocannabinol

(+/-)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether

Refernces

• 1、 Siegel,Gordon,Razdan. "Studies on the synthesis of (-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC) and related compounds: An improved oxidative procedure". . p. 851 - 853. Retrieved 2007/10/02.