(15R)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene

Base Information

• Chemical Name: (15R)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene
• CAS No.: 137064-49-4
• Molecular Formula: C₂₉H₃₅NO₆
• Molecular Weight: 493.6
• Mol file: 137064-49-4.mol

Synonyms:

Chemical Property of (15R)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (15R)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene

There total 12 articles about (15R)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene 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: 70.2%

(15S)-12-acetyl-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene (137064-45-0) → (15S)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene (137064-49-4,137064-50-7)

Guidance literature:

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; Heating;

DOI:10.1246/bcsj.64.2855

Reference yield: 59.3%

(15R)-12-acetyl-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene (137064-48-3) → (15R)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene (137064-49-4,137064-50-7)

Guidance literature:

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; for 3h; Heating;

DOI:10.1246/bcsj.64.2855

Reference yield:

ar-abietatriene (19407-28-4) → (15S)-12-acetoxy-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene (137064-49-4,137064-50-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 23.358 g / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 4 h / Heating

2: 1.) BH₃*THF, 2.) H₂O₂, aq. NaOH / 1.) THF, 0-5 deg C, 3 h, 2a.) THF, -5 - 0 deg C, 30 min, 2b.) 1.5 h, r. t.

3: 93 percent / pyridine / 2.5 h / 80 - 85 °C

4: AlCl₃ / nitrobenzene / 1.) 0-5 deg C, 30 min, 2.) 1.5 h, r. t.

5: 70.2 percent / m-chloroperbenzoic acid, p-TsOH / 1,2-dichloro-ethane / Heating

With pyridine; sodium hydroxide; aluminium trichloride; borane-THF; dihydrogen peroxide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; nitrobenzene; 1,2-dichloro-ethane;

DOI:10.1246/bcsj.64.2855

upstream raw materials:

(15S)-12-acetyl-16-(4-nitrobenzoyloxy)-8,11,13-abietatriene

ar-abietatriene

4-nitro-benzoyl chloride

(+)-8,11,13,15-abietatetraene