Fmoc-D-glutamic acid α-allyl ester

Base Information

• Chemical Name: Fmoc-D-glutamic acid α-allyl ester
• CAS No.: 204251-86-5
• Molecular Formula: C23H23NO6
• Molecular Weight: 409.43182
• Hs Code.: 2924299090
• Mol file: 204251-86-5.mol

Synonyms:Fmoc-D-glutamic acid α-allyl ester;Moc-D-Glu-Oall;(R)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)-amino)-5-(allyloxy)-5-oxopentanoic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamic acid 1-(2-propenyl) ester;N-Fmoc-D-glutamic acid 1-allyl ester

Chemical Property of Fmoc-D-glutamic acid α-allyl ester

Chemical Property:

• PSA: 101.93000
• LogP: 3.87860
• Storage Temp.: 2-8°C

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-d-glu-oall ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Fmoc-D-glutamic acid α-allyl ester

There total 8 articles about Fmoc-D-glutamic acid α-allyl 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: 96.0%

(R)-1-allyl 5-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pentanedioate → (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid (204251-86-5)

Guidance literature:

With trifluoroacetic acid; at 0 - 20 ℃; for 8h;

DOI:10.1002/anie.201410270

Reference yield: 91.0%

Fmoc-Glu(OtBu)-OH (104091-08-9) + allyl bromide (106-95-6) → (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid (204251-86-5)

Guidance literature:

Fmoc-Glu(OtBu)-OH; With caesium carbonate; In methanol; water; pH=8;

allyl bromide; In acetonitrile; at 20 ℃; for 21h;

With trifluoroacetic acid; In dichloromethane; for 0.833333h;

DOI:10.1039/c0cc04670a

Reference yield:

Fmoc-Glu(OtBu)-OH (104091-08-9) → (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid (204251-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / 1-hydroxybenzotriazole, benzotriazole-1-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate, diisopropylethylamine / 15 h

2: 89 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja9839769

upstream raw materials:

Fmoc-Glu(OtBu)-OH

allyl bromide

(R)-1-allyl 5-tert-butyl 2-((tertbutoxycarbonyl)amino)pentanedioate

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

c(kVHypLfPHKNq)

c(IVHypLfPVKNq)