Fmoc-3-iodo-L-tyrosine

Base Information

• Chemical Name: Fmoc-3-iodo-L-tyrosine
• CAS No.: 134486-00-3
• Molecular Formula: C24H20 I N O5
• Molecular Weight: 529.331
• European Community (EC) Number: 695-207-1
• DSSTox Substance ID: DTXSID20446663
• Nikkaji Number: J1.351.440B
• Wikidata: Q82265377
• Mol file: 134486-00-3.mol

Synonyms:Fmoc-3-iodo-L-tyrosine;134486-00-3;Fmoc-3-iodo-Tyr-OH;Fmoc-Tyr(3-I)-OH;Fmoc-L-Tyr(3-I)-OH;L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-3-iodophenyl)propanoic acid;C24H20INO5;SCHEMBL2030857;SCHEMBL14584328;DTXSID20446663;MFCD00235906;AKOS015837217;AKOS015907961;AC-27954;AS-10396;CS-0100996;E70515;EN300-7363350;J-006545;L-Tyrosine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-iodo-;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-3-iodo-tyrosine;N-(9H-Fluorene-9-ylmethoxycarbonyl)-3-iodo-4-hydroxy-L-phenylalanine;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxy-3-iodophenyl)propanoic acid;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid

Chemical Property of Fmoc-3-iodo-L-tyrosine

Chemical Property:

• Boiling Point: 675.7±55.0 °C(Predicted)
• PKA: 2.86±0.10(Predicted)
• PSA: 95.86000
• Density: 1.634±0.06 g/cm3(Predicted)
• LogP: 4.92210
• Storage Temp.: 2-8°C
• Solubility.: DMF (Slightly), Methanol (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 529.03862
• Heavy Atom Count: 31
• Complexity: 624

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-3-iodo-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=C(C=C4)O)I)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=C(C=C4)O)I)C(=O)O
• Uses: Fmoc-3-iodo-l-tyrosine acts as a reagent in the synthesis of antitumor rubiyunnanin B dityrosine core by Suzuki coupling.

Technology Process of Fmoc-3-iodo-L-tyrosine

There total 2 articles about Fmoc-3-iodo-L-tyrosine 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: 93.0%

N-Fmoc-Tyr-OH (112883-29-1,92954-90-0) → (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-3-iodophenyl)propionic acid (134486-00-3,244028-70-4)

Guidance literature:

With tetrafluoroboric acid; Barluenga reagent; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1039/b003064n

Reference yield: 82.0%

3-Iodo-L-tyrosine (70-78-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-3-iodophenyl)propionic acid (134486-00-3,244028-70-4)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; acetone; at 20 ℃;

DOI:10.1021/jm050376t

Reference yield:

C28H29N2O4Pol + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Gln(Trt)-OH + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4) + Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) + (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-3-iodophenyl)propionic acid (134486-00-3,244028-70-4) + (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid (133174-15-9) + Fmoc-Lys(ivDde)-OH (204777-78-6) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) + Fmoc-Glu(ODmab)-OH → C67H100IN21O21S2

Guidance literature:

C₂₈H₂₉N₂O₄Pol; With piperidine; In N,N-dimethyl-formamide; Rink amide MBHA resin

Fmoc-Lys(ivDde)-OH; With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 2.5h; Rink amide MBHA resin

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Gln(Trt)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-Thr(tBu)-OH; (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-3-iodophenyl)propionic acid; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Fmoc-Glu(ODmab)-OH; Further stages;

upstream raw materials:

N-Fmoc-Tyr-OH

3-Iodo-L-tyrosine

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

Refernces

• 1、 Moore, Sandra Blaj,Van Der Hoek, Joost,De Capua, Antonia,Van Koetsveld, Peter M.,Hofland, Leo J.,Lamberts, Steven W. J.,Goodman, Murray,Taulane, Joseph P.. "Discovery of iodinated somatostatin analogues selective for hsst2 and hsst5 with excellent inhibition of growth hormone and prolactin release from rat pituitary cells". . p. 6643 - 6652. Retrieved 2007/10/03.