NALPHA-FMOC-L-THREONINE TERT-BUTYL ESTER

Base Information

• Chemical Name: NALPHA-FMOC-L-THREONINE TERT-BUTYL ESTER
• CAS No.: 120791-76-6
• Molecular Formula: C23H27 N O5
• Molecular Weight: 397.471
• Mol file: 120791-76-6.mol

Synonyms:Fmoc-Thr-OBu-t

Chemical Property of NALPHA-FMOC-L-THREONINE TERT-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100 °C
• Refractive Index: 1.569
• Boiling Point: 591.083°C at 760 mmHg
• Flash Point: 311.276°C
• PSA: 84.86000
• Density: 1.197g/cm³
• LogP: 4.00710
• Storage Temp.: Refrigerator
• Solubility.: soluble in Chloroform

Purity/Quality:

98%, ^*data from raw suppliers

Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-threonine tert-Butyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of NALPHA-FMOC-L-THREONINE TERT-BUTYL ESTER

There total 9 articles about NALPHA-FMOC-L-THREONINE TERT-BUTYL 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: 94.0%

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxy-butyric acid tert-butyl ester (600173-01-1) → N-fluorenylmethoxycarbonyl-threonine-tert-butyl ester (120791-76-6)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo0344891

Reference yield: 82.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + Fmoc-Thr-OH (73731-37-0) → N-fluorenylmethoxycarbonyl-threonine-tert-butyl ester (120791-76-6)

Guidance literature:

In cyclohexane; ethyl acetate; at 20 ℃; for 94h; Inert atmosphere;

DOI:10.1016/j.tet.2019.130776

Reference yield: 77.0%

Fmoc-Thr-OH (73731-37-0) + tert-butyl alcohol (75-65-0) → N-fluorenylmethoxycarbonyl-threonine-tert-butyl ester (120791-76-6)

Guidance literature:

With dicyclohexyl-carbodiimide; copper(l) chloride;

DOI:10.1002/anie.199706181

upstream raw materials:

O-(Acetoacetyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonin-tert-butylester

Fmoc-Thr-OH

tert-butyl alcohol

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxy-butyric acid tert-butyl ester

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-O-(4,6-di-O-acetyl-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-3-thio-α-D-galactopyranosyl)-L-threonine tert-butyl ester

C₅₂H₆₂N₂O₁₉

N-fluorenylmethoxycarbonyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine tert-butyl ester

Ac-Asp-Glu-Gly-Glu-Glu-Thr-Phe-OH

Refernces

• 1、 -. "Polypeptide raw material N-fluorenylmethoxycarbonyl-O-tert-butyl threonine preparation method". Paragraph 0012-0015. . Retrieved 2019/01/23.
• 2、 Stra?burger, David,Glaffig, Markus,Stergiou, Natascha,Bialas, Sabrina,Besenius, Pol,Schmitt, Edgar,Kunz, Horst. "Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity". . p. 1142 - 1146. Retrieved 2018/10/21.