5-[3,5-DIMETHOXY-4-(FMOC-AMINOMETHYL)PHENOXY]PENTANOIC ACID

Base Information

• Chemical Name: 5-[3,5-DIMETHOXY-4-(FMOC-AMINOMETHYL)PHENOXY]PENTANOIC ACID
• CAS No.: 115109-65-4
• Molecular Formula: C29H31 N O7
• Molecular Weight: 505.56
• Mol file: 115109-65-4.mol

Synonyms:Fmoc-PAL

Chemical Property of 5-[3,5-DIMETHOXY-4-(FMOC-AMINOMETHYL)PHENOXY]PENTANOIC ACID

Chemical Property:

• Vapor Pressure: 1.48E-22mmHg at 25°C
• Melting Point: 178-180℃
• Boiling Point: 733°Cat760mmHg
• Flash Point: 397.1°C
• PSA: 103.32000
• Density: 1.238g/cm³
• LogP: 5.76710
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

Fmoc-PAL ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: It is a reagent for the mild solid-phase synthesis of C-terminal peptide amides. Used in the solid-phase peptide synthesis (SPPS).

Technology Process of 5-[3,5-DIMETHOXY-4-(FMOC-AMINOMETHYL)PHENOXY]PENTANOIC ACID

There total 13 articles about 5-[3,5-DIMETHOXY-4-(FMOC-AMINOMETHYL)PHENOXY]PENTANOIC ACID 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:

ethyl 5'-(4-formyl-3,5-dimethoxyphenoxy)valerate (115109-57-4) → 5-<4-<<(Fmoc)amino>methyl>-3,5-dimethoxyphenoxy>valeric acid (115109-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) molecular sieves 3A, 2.) NaBH₃CN / 1.) MeOH, reflux, 6 h, 2.) 2 h

2: 70 percent / ammonium formate, H₂ / 10percent Pd/C / ethanol / 50 h / 25 °C

3: 1.) 2N aq. NaOH / 1.) dioxane, 25 deg C, 2 h, 2.) dioxane, 25 deg C, 2 h

With sodium hydroxide; 3 A molecular sieve; hydrogen; ammonium formate; sodium cyanoborohydride; palladium on activated charcoal; In ethanol;

DOI:10.1021/jo00070a041

Reference yield:

ethyl 5-bromovalerate (14660-52-7) → 5-<4-<<(Fmoc)amino>methyl>-3,5-dimethoxyphenoxy>valeric acid (115109-65-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) KOtBu / 1.) DMF, 25 deg C, 2.) 110 deg C, 5h

2: 4N aq. NaOH / methanol / 1 h / 25 °C

3: 95 percent / NH₂OH, Na₂CO₃ / H₂O / 2 h

4: 96 percent / H₂ / 10percent Pd/C / aq. acetic acid / 2 h / 25 °C / 2280 Torr

5: aq. Na₂CO₃ / dioxane / 3 h / 25 °C

With sodium hydroxide; potassium tert-butylate; hydrogen; hydroxylamine; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; water; acetic acid;

DOI:10.1021/jo00299a011

Reference yield:

syringaldehyde (22080-96-2) → 5-<4-<<(Fmoc)amino>methyl>-3,5-dimethoxyphenoxy>valeric acid (115109-65-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) KOtBu / 1.) DMF, 25 deg C, 2.) 110 deg C, 5h

2: 4N aq. NaOH / methanol / 1 h / 25 °C

3: 95 percent / NH₂OH, Na₂CO₃ / H₂O / 2 h

4: 96 percent / H₂ / 10percent Pd/C / aq. acetic acid / 2 h / 25 °C / 2280 Torr

5: aq. Na₂CO₃ / dioxane / 3 h / 25 °C

With sodium hydroxide; potassium tert-butylate; hydrogen; hydroxylamine; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; water; acetic acid;

DOI:10.1021/jo00299a011

upstream raw materials:

(9H-fluoren-9-yl)methyl azidoformate

5-(4-aminomethyl-3,5-dimethoxyphenoxy)valeric acid acetate

ethyl 5-(4-aminomethyl-3,5-dimethoxyphenoxy)valerate acetate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Refernces

• 1、 Albericio,Kneib-Cordonier,Biancalana,Gera,Masada,Hudson,Barany. "Preparation and application of the 5-(4-(9-fluorenylmethyloxycarbonyl) aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditions1-3". . p. 3730 - 3743. Retrieved 2007/10/02.