N-FMOC-L-THREONINE PENTAFLUOROPHENYL ESTER)

Base Information

• Chemical Name: N-FMOC-L-THREONINE PENTAFLUOROPHENYL ESTER)
• CAS No.: 86061-06-5
• Molecular Formula: C25H18 F5 N O5
• Molecular Weight: 507.414
• Mol file: 86061-06-5.mol

Synonyms:L-Threonine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, pentafluorophenyl ester (9CI);N-(9-Fluorenylmethoxycarbonyl)threonine pentafluorophenyl ester

Chemical Property of N-FMOC-L-THREONINE PENTAFLUOROPHENYL ESTER)

Chemical Property:

• PSA: 84.86000
• LogP: 4.96650

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-FMOC-L-THREONINE PENTAFLUOROPHENYL ESTER)

There total 3 articles about N-FMOC-L-THREONINE PENTAFLUOROPHENYL ESTER) 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: 99.0%

O-tert-butyl-Nα-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (117088-31-0) → Nα-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (86061-06-5)

Guidance literature:

With trifluoroacetic acid; for 0.75h; Ambient temperature;

Reference yield: 77.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-Thr-OH (73731-37-0) → Nα-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (86061-06-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; 0 deg C, 1 h; r.t., 1 h;

DOI:10.1055/s-1983-30327

Reference yield:

(9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → Nα-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester (86061-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaHCO₃ / H₂O; acetone / Ambient temperature

2: dicyclohexylcarbodiimide / ethyl acetate / 2 h / 0 °C

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In water; ethyl acetate; acetone;

upstream raw materials:

2,3,4,5,6-pentafluorophenol

Fmoc-Thr-OH

O-tert-butyl-N^α-(fluoren-9-ylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

(9-fluorenyl)methyl pentafluorophenyl carbonate

Downstream raw materials:

N^α-(fluoren-9-ylmethoxycarbonyl)-O-<3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl>-L-threonine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-3-O-<2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>3)-4,6-di-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl>-L-threonine pentafluorophenyl ester

C₅₆H₇₇N₉O₁₅S₂

N^α-(Fluoren-9-ylmethoxycarbonyl)-O-<3,4,6-tri-O-acetyl-2-O-<2,3,4-tri-O-benzoyl-6-O-bis-(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranosyl>-α-D-mannopyranosyl>-L-threonine pentafluorophenyl Ester

Refernces

• 1、 Liu, Mian,Young Jr., Victor G.,Lohani, Sachin,Live, David,Barany, George. "Syntheses of TN building blocks Nα-(9- fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D- galactopyranosyl)-L-serine/L-threonine pentafluorophenyl esters: Comparison of protocols and elucidation of side reactions". . p. 1273 - 1285. Retrieved 2007/10/03.
• 2、 Jansson, Anita Ma.,Meldal, Morten,Back, Klaus. "The active ester N-fmoc-3-O-[Ac4-α-D-Manp-(1→2)-Ac 3-α-D-Manp-1-]=thre-O-Pfp as a building block in solid-phase synthesis of an o-linked dimannosyl glycopeptide". . p. 6991 - 6994. Retrieved 2007/12/18.