Fmoc-D-Glu(OBzl)-OH

Base Information

• Chemical Name: Fmoc-D-Glu(OBzl)-OH
• CAS No.: 104091-11-4
• Molecular Formula: C27H25NO6
• Molecular Weight: 459.499
• DSSTox Substance ID: DTXSID30445581
• Wikidata: Q72478608
• Mol file: 104091-11-4.mol

Synonyms:Fmoc-D-Glu(OBzl)-OH;104091-11-4;Fmoc-D-Glu(Bzl)-OH;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanoic acid;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-phenylmethoxypentanoic acid;Fmoc-D-glutamic acid |A-benzyl ester;Fmoc-L-glutamic acid |A benzyl ester;DTXSID30445581;MFCD00273449;AKOS016842928;FD21366;AS-49051;CS-0101002;EN300-7365631;J-300099;Q-101686;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-glutamic-acid-gamma-benzyl ester;(2R)-5-(benzyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-oxopentanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(benzyloxy)-5-oxopentanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-glutamic-acid-gamma-benZyl ester (Fmoc-D-Glu(OBZl)-OH)

Chemical Property of Fmoc-D-Glu(OBzl)-OH

Chemical Property:

• Boiling Point: 698.2±55.0 °C(Predicted)
• PKA: 3.70±0.10(Predicted)
• PSA: 101.93000
• Density: 1.289±0.06 g/cm3(Predicted)
• LogP: 4.89280
• Storage Temp.: Store at RT.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 459.16818752
• Heavy Atom Count: 34
• Complexity: 683

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-D-glutamic acid γ-benzyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)CCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)CC[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-D-Glu(OBzl)-OH

There total 2 articles about Fmoc-D-Glu(OBzl)-OH 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: 45.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + D-glutamic acid-5-benzyl ester (2578-33-8,1676-73-9,29456-09-5,25014-27-1) → N-Fmoc-D-Glu γ-benzyl ester (104091-11-4)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; Ambient temperature;

DOI:10.1248/cpb.47.194

Reference yield:

N-Fmoc-D-glutamic acid (104091-09-0) + benzyl alcohol (100-51-6,185532-71-2) → (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanoic acid (104091-10-3) + N-Fmoc-D-Glu γ-benzyl ester (104091-11-4)

Guidance literature:

With potassium carbonate; dicyclohexyl-carbodiimide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 23 h, 2.) THF, 3.5 h;

DOI:10.1021/jo00374a019

Reference yield:

Fmoc-Leu-OH (35661-60-0) + C21H20NO5Pol + N-(9-fluorenylmethoxycarbonyl)-D-leucine (35661-60-0,126727-03-5,114360-54-2) + (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine (130674-54-3) + Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether (71989-33-8,128107-47-1) + N-Fmoc-D-Glu γ-benzyl ester (104091-11-4) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) + (R)-3-[(tert-butyldimethylsilyl)oxy]decanoic acid → C68H117N8O16PolSi

Guidance literature:

C₂₁H₂₀NO₅Pol; With piperidine; In 1-methyl-pyrrolidin-2-one; 2-chlorotrityl chloride resin Automated synthesizer;

Fmoc-Leu-OH; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.666667h; 2-chlorotrityl chloride resin Automated synthesizer;

Fmoc-Leu-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine; Nα-(9-fluorenylmethoxycarbonyl)-D-serine-tert-butyl ether; N-Fmoc-D-Glu γ-benzyl ester; N-(9-fluorenylmethoxycarbonyl)-D-valine; (R)-3-[(tert-butyldimethylsilyl)oxy]decanoic acid; Further stages;

DOI:10.1002/psc.2852

upstream raw materials:

N-Fmoc-D-glutamic acid

benzyl alcohol

(fluorenylmethoxy)carbonyl chloride

D-glutamic acid-5-benzyl ester

Refernces

• 1、 Kelly, Robert C.,Gebhard, I.,Wicnienski, N.. "Synthesis of (R)- and (S)-(glu)Thz and the Corresponding Bisthiazole Dipeptide of Dolastatin 3". . p. 4590 - 4594. Retrieved 2007/10/02.