(+)-dibenzoylpederin

Base Information

• Chemical Name: (+)-dibenzoylpederin
• CAS No.: 123483-10-3
• Molecular Formula: C₃₉H₅₃NO₁₁
• Molecular Weight: 711.85
• Mol file: 123483-10-3.mol

Synonyms:(+)-dibenzoylpederin

Chemical Property of (+)-dibenzoylpederin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-dibenzoylpederin

There total 13 articles about (+)-dibenzoylpederin 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: 92.0%

(+)-pederine (27973-72-4) + benzoyl chloride (98-88-4) → (+)-dibenzoylpederin (123483-10-3)

Guidance literature:

With dmap; In pyridine; for 5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86075-0

Reference yield:

(2S,4R,6R)-4-Benzoyloxy-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-carboxylic acid (85708-35-6) → (+)-dibenzoylpederin (123483-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 15.9 mg / PyBOP; HOBt; i-Pr₂NEt / NH₄Cl / dimethylformamide / 1.5 h / 20 °C

2: CH₂Cl₂ / 17 h / 20 °C

3: Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

4: 8.53 mg / NaBH₄ / ethanol / 0.5 h / -20 °C

With sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; ammonium chloride; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)00635-X

Reference yield:

Benzoic acid (2R,4R,6S)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester → (+)-dibenzoylpederin (123483-10-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Jones reagent / acetone / 0 - 20 °C

2: 15.9 mg / PyBOP; HOBt; i-Pr₂NEt / NH₄Cl / dimethylformamide / 1.5 h / 20 °C

3: CH₂Cl₂ / 17 h / 20 °C

4: Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

5: 8.53 mg / NaBH₄ / ethanol / 0.5 h / -20 °C

With sodium tetrahydroborate; jones reagent; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; ammonium chloride; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Jones oxidation;

DOI:10.1016/S0040-4020(02)00635-X

upstream raw materials:

C₄₅H₅₉NO₁₁Se

Benzoic acid (S)-chlorocarbonyl-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

(+/-)-benzoylselenopederic acid

(αS,2R,4R,5R,6R)-N-<(S)-<(2S,4R,6R)-4-(benzoyloxy)-6-<(S)-2,3-dimethoxypropyl>-tetrahydro-5,5-dimethyl-2H-pyran-2-yl>methoxymethyl>-α-(benzoyloxy)tetrahydro-2-methoxy-5,6-dimethyl-4-<(phenylseleno)methyl>-2H-pyran-2-acetamide

Downstream raw materials:

(+)-pederine

(+/-)-pederin

Refernces

• 1、 Willson, Timothy M.,Kocienski, Philip,Jarowicki, Krzysztof,Isaac, Kim,Hitchcock, Peter M.,Faller, Andrew,Campbell, Simon F.. "Studies related to the synthesis of pederin. Part 2. Synthesis of pederol dibenzoate and benzoylpedamide". . p. 1767 - 1782. Retrieved 2007/10/02.
• 2、 Willson, Timothy,Kocienski, Philip,Faller, Andrew,Campbell, Simon. "The Total Synthesis of (+/-)-Pederin". . p. 106 - 108. Retrieved 2007/10/02.