FMOC-PRO-OSU

Base Information

• Chemical Name: FMOC-PRO-OSU
• CAS No.: 109074-94-4
• Molecular Formula: C24H22 N2 O6
• Molecular Weight: 434.448
• Mol file: 109074-94-4.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 2-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-, 9H-fluoren-9-ylmethylester, (S)- (9CI)

Chemical Property of FMOC-PRO-OSU

Chemical Property:

• Refractive Index: 1.668
• Boiling Point: 604.8±65.0 °C(Predicted)
• PKA: -4.05±0.40(Predicted)
• PSA: 93.22000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 2.88290
• Storage Temp.: Store at 0°C

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-L-proline N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-PRO-OSU

There total 1 articles about FMOC-PRO-OSU 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: 90.6%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Fmoc-Pro-OH (71989-31-6) → O2-(2,5-dioxopyrrolidin-1-yl) O1-(9H-fluoren-9-ylmethyl) (2S)-pyrrolidine-1,2-dicarboxylate (109074-94-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 12h;

Reference yield: 72.5%

1-(4-methoxyphenyl)-3-methylpiperazin-2-one hydrochloride + O2-(2,5-dioxopyrrolidin-1-yl) O1-(9H-fluoren-9-ylmethyl) (2S)-pyrrolidine-1,2-dicarboxylate (109074-94-4) → 1-(4-methoxyphenyl)-3-methyl-4-L-prolylpiperazin-2-one

Guidance literature:

1-(4-methoxyphenyl)-3-methylpiperazin-2-one hydrochloride; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

O₂-(2,5-dioxopyrrolidin-1-yl) O₁-(9H-fluoren-9-ylmethyl) (2S)-pyrrolidine-1,2-dicarboxylate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

With diethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

O2-(2,5-dioxopyrrolidin-1-yl) O1-(9H-fluoren-9-ylmethyl) (2S)-pyrrolidine-1,2-dicarboxylate (109074-94-4) → Pro-Ser(O-t-Bu)-Tyr(O-t-Bu)-OAll

Guidance literature:

Multi-step reaction with 3 steps

1: 570 mg / DIPEA / dimethylformamide / 17 h / 0 - 20 °C

2: 194 g / BOP; DIPEA / CH₂Cl₂ / 72 h

3: Et₂NH / acetonitrile / 0.5 h / 20 °C

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Condensation / 3: Substitution;

DOI:10.1021/jo991523w

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Fmoc-Pro-OH

Downstream raw materials:

Fmoc-Pro-Ser(O-t-Bu)-Tyr(O-t-Bu)-OAll

Lys(ε-Boc)-Pro-Ser(O-t-Bu)-Tyr(O-t-Bu)-OAll

Fmoc-Lys(ε-Boc)-Pro-Ser(O-t-Bu)-Tyr(O-t-Bu)-OAll

Fmoc-Ala-Lys(ε-Boc)-Pro-Ser(O-t-Bu)-Tyr(O-t-Bu)-OH

Refernces

• 1、 Yang, Jinhua,Wang, Changliu,Yao, Chaochao,Chen, Chunqiu,Hu, Yafang,He, Guifeng,Zhao, Junfeng. "Site-Specific Incorporation of Multiple Thioamide Substitutions into a Peptide Backbone via Solid Phase Peptide Synthesis". . p. 1484 - 1494. Retrieved 2020/01/02.