(-)-PF₁₁₆₃B

Base Information

• Chemical Name: (-)-PF₁₁₆₃B
• CAS No.: 258871-60-2
• Molecular Formula: C₂₇H₄₃NO₅
• Molecular Weight: 461.642
• Mol file: 258871-60-2.mol

Synonyms:

Chemical Property of (-)-PF₁₁₆₃B

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

PF-1163B ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-PF₁₁₆₃B

There total 32 articles about (-)-PF₁₁₆₃B 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: 50.0%

9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-6-methyl-tetradecanoic acid tert-butyl ester (259738-80-2) → (-)-PF1163B (258871-60-2)

Guidance literature:

9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-6-methyl-tetradecanoic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.583333h;

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 0 ℃; for 48h;

DOI:10.1055/s-0037-1610694

Reference yield:

(6R,9R)-9-{(S)-3-[4-(2-Hydroxy-ethoxy)-phenyl]-2-methylamino-propionyloxy}-6-methyl-tetradecanoic acid → (-)-PF1163B (258871-60-2)

Guidance literature:

With TEA; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; In dichloromethane; at 0 ℃; for 48h;

DOI:10.7164/antibiotics.52.1146

Reference yield:

(4R)-4-methyl-6-hydroxyhexan-1-al (180908-43-4) → (-)-PF1163B (258871-60-2)

Guidance literature:

Multi-step reaction with 13 steps

1: toluene / 3 h / 100 °C

2: H₂ / Pd/C / ethanol / 3 h

3: PCC; AcONa / CH₂Cl₂ / 3 h / 20 °C

4: PhLi / tetrahydrofuran / 4 h / -78 - 20 °C

5: Cl₂CHCO₂H / CH₂Cl₂ / 2 h / 0 °C

6: 72 percent / [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)] / diethyl ether / 2 h / -78 °C

7: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8: 71 percent / O₃; Ph₃P / CH₂Cl₂ / 0.25 h / -78 °C

9: sec-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C

10: H₂ / Pd(OH)2 / methanol / 15 h / 20 °C

11: DMAP / toluene / 3 h / 20 °C

12: 95 percent TFA / CH₂Cl₂ / 2 h / 20 °C

13: bis(2-oxo-3-oxazolidinyl)phosphinic chloride; TEA / CH₂Cl₂ / 48 h / 0 °C

With 2,6-dimethylpyridine; dichloro-acetic acid; dmap; [CpTiCl((S,S)-2,3-Me₂CO₂-1,1,4,4-Ph₄-1,4-butanediolato)]; TEA; hydrogen; sec.-butyllithium; sodium acetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; ozone; phenyllithium; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; 1: Wittig olefination / 2: Catalytic hydrogenation / 3: Oxidation / 4: Wittig olefination / 5: vinyl ether cleavage / 6: Alkylation / 7: silylation / 8: ozonolysis / 9: Wittig olefination / 10: Catalytic hydrogenation / 11: Esterification / 12: desilylation; Boc deprotection; ester cleavage / 13: Cyclization;

DOI:10.7164/antibiotics.52.1146

upstream raw materials:

(4R)-4-methyl-6-hydroxyhexan-1-al

(3R)-citronellol

Boc-Tyr-OH

tert-butyl (6R)-8-hydroxy-6-methyloctanoate

Refernces

• 1、 Tatsuta,Takano,Ikeda,Nakano,Miyazaki. "The total synthesis and absolute structure of antifungal antibiotics (-)-PF1163A and B". . p. 1146 - 1151. Retrieved 2007/10/03.