(6aR-trans)-1-[(tert-Butyl)diMethylsilyloxy]-6a,7,8

Base Information

• Chemical Name: (6aR-trans)-1-[(tert-Butyl)diMethylsilyloxy]-6a,7,8
• CAS No.: 138285-36-6
• Molecular Formula: C27H42O3Si
• Molecular Weight: 442.714
• Mol file: 138285-36-6.mol

Synonyms:(6aR-trans)-1-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-6a,7,8,10a-tetrahydro-6,6-diMethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylate;1-O-[(tert-Butyl)diMethylsilyloxy]-9-forMyl-9-tetrahydro Cannabinol

Chemical Property of (6aR-trans)-1-[(tert-Butyl)diMethylsilyloxy]-6a,7,8

Chemical Property:

• PSA: 35.53000
• LogP: 7.59320

Purity/Quality:

98% ^*data from raw suppliers

1-O-[(tert-Butyl)dimethylsilyloxy]-9-formyl-delta9-tetrahydro cannabinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (6aR,10aR)-1-[tert-butyl(dimethyl)silyl]oxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carbaldehyde is used in the preparation of a major Tetrahydrocannabinol (T293200) metabolite.

Technology Process of (6aR-trans)-1-[(tert-Butyl)diMethylsilyloxy]-6a,7,8

There total 8 articles about (6aR-trans)-1-[(tert-Butyl)diMethylsilyloxy]-6a,7,8 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 tert-butyldimethylsilyl ether

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

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

11-nor-9-carboxt-Δ-9-tetrahydrocannabinol

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.