Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbon yl]amino]ethyl]-

Base Information

• Chemical Name: Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbon yl]amino]ethyl]-
• CAS No.: 143192-34-1
• Molecular Formula: C₂₄H₂₈N₂O₆
• Molecular Weight: 440.496
• Mol file: 143192-34-1.mol

Synonyms:{tert-Butoxycarbonyl-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-amino}-acetic acid;9-fluorenylmethoxycarbonyl-N-(2-aminoethyl)-Boc-glycine;

Chemical Property of Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbon yl]amino]ethyl]-

Chemical Property:

• PSA: 105.17000
• LogP: 4.23770

Purity/Quality:

≥98%, ^*data from raw suppliers

Boc-Aeg(Fmoc)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbon yl]amino]ethyl]-

There total 7 articles about Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-[2-[[(9H-fluoren-9-ylmethoxy)carbon yl]amino]ethyl]- 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%

benzyl 2-((2-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethyl)(tert-butoxycarbonyl)amino)acetate (1181810-80-9) → 9-fluorenylmethoxycarbonyl-N-(2-aminoethyl)-Boc-glycine (143192-34-1)

Guidance literature:

With 5% Pd(II)/C(eggshell); hydrogen; In methanol; for 2.5h;

DOI:10.1021/ja904712t

Reference yield:

tert-butyl N-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl)glycinate (169396-89-8) → 9-fluorenylmethoxycarbonyl-N-(2-aminoethyl)-Boc-glycine (143192-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA

2: acetone; H₂O

With trifluoroacetic acid; In water; acetone;

DOI:10.1002/1521-3773(20010716)40:14<2631::AID-ANIE2631>3.0.CO;2-6

Reference yield:

benzyl N-[2-((fluorenylmethoxycarbonyl)amino)ethyl]glycinate (791778-61-5) + di-tert-butyl dicarbonate (24424-99-5) → 9-fluorenylmethoxycarbonyl-N-(2-aminoethyl)-Boc-glycine (143192-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h

2: 5% Pd(II)/C(eggshell); hydrogen / methanol / 2.5 h

With 5% Pd(II)/C(eggshell); hydrogen; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/ja904712t

upstream raw materials:

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

di-tert-butyl dicarbonate

N-[2'-(N'-(9-fluorenylmethyloxycarbonyl)-amino)ethyl]glycine

tert-butyl N-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl)glycinate

Refernces

• 1、 Heemstra, Jennifer M.,Liu, David R.. "Templated synthesis of peptide nucleic acids via sequence-selective base-filling reactions". . p. 11347 - 11349. Retrieved 2011/03/21.
• 2、 Byk, Gerardo,Gilon, Chaim. "Building Units for N-Backbone Cyclic Peptides. 1. Synthesis of Protected N-(ω-Aminoalkylene)amino Acids and Their Incorporation into Dipeptide Units". . p. 5687 - 5692. Retrieved 2007/10/02.