L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester

Base Information

• Chemical Name: L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester
• CAS No.: 143674-78-6
• Molecular Formula: C27H25NO5
• Molecular Weight: 443.499
• Mol file: 143674-78-6.mol

Synonyms:O-allyl-N-Fmoc-L-tyrosine-OH;Fmoc-Tyr-OAll;Nα-Fmoc-tyrosine allyl ester;Fmoc-Tyr-OAllyl;N-Fmoc-L-tyrosine allyl ester;(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-phenyl)-propionic acid allyl ester;Fmoc-Tyr-O-allyl;

Chemical Property of L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester

Chemical Property:

• PSA: 84.86000
• LogP: 4.96210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester

There total 10 articles about L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl 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: 100.0%

allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoate (208655-83-8) → (S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate (143674-78-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/psc.2508

Reference yield: 91.0%

N-Fmoc-Tyr-OH (112883-29-1,92954-90-0) + allyl bromide (106-95-6) → (S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate (143674-78-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 15 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201602047

Reference yield:

Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) → (S)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanoate (143674-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Cs₂CO₃ / dimethylformamide / 2 h

2: 70percent TFA / CH₂Cl₂ / 0.25 h

With caesium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)00558-9

upstream raw materials:

N-Fmoc-Tyr-OH

allyl bromide

allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoate

Fmoc-Tyr(tBu)-OH