N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine

Base Information

• Chemical Name: N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine
• CAS No.: 150308-80-8
• Molecular Formula: C26H25NO5Se
• Molecular Weight: 510.448
• DSSTox Substance ID: DTXSID00933905
• Nikkaji Number: J1.615.005C
• Wikidata: Q72478671
• Mol file: 150308-80-8.mol

Synonyms:Fmoc-Sec(MBzl)-OH;N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine

Chemical Property of N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine

Chemical Property:

• Boiling Point: 708.5±60.0 °C(Predicted)
• PKA: 3.50±0.10(Predicted)
• PSA: 88.35000
• LogP: 4.78040
• Storage Temp.: Store at +2°C to +8°C.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 511.08979
• Heavy Atom Count: 33
• Complexity: 631

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-Sec(Mob)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C[Se]CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: COC1=CC=C(C=C1)C[Se]C[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine

There total 17 articles about N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine 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%

Fmoc-(Se)-p-methoxybenzylselenocysteine-OAll (342904-13-6) → N-(9-fluorenylmethoxycarbonyl)-Se-(p-methoxyphenylmethyl)-L-selenocysteine (150308-80-8)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 1h;

DOI:10.1021/ol015712o

Reference yield: 97.0%

Fmoc-Sec(Mob)-OMe (1365284-58-7) → N-(9-fluorenylmethoxycarbonyl)-Se-(p-methoxyphenylmethyl)-L-selenocysteine (150308-80-8)

Guidance literature:

With trimethyltin(IV) hydroxide; In 1,2-dichloro-ethane; for 1h; Inert atmosphere; Reflux;

DOI:10.1002/psc.1430

Reference yield: 89.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Se-(4-methoxybenzyl)-L-selenocysteine (146552-76-3) → N-(9-fluorenylmethoxycarbonyl)-Se-(p-methoxyphenylmethyl)-L-selenocysteine (150308-80-8)

Guidance literature:

With triethylamine; In water; acetonitrile; for 1h; Ambient temperature;

DOI:10.1248/cpb.41.502

upstream raw materials:

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

Se-(4-methoxybenzyl)-L-selenocysteine

Fmoc-(Se)-p-methoxybenzylselenocysteine-OAll

1,2-bis(4-methoxybenzyl)diselane

Downstream raw materials:

H-MEELYKSG(¹³C-1)U-NH₂

H-MEELYKSG(¹³C-1)U-OH

H-DTHFPICIFCCGU-NH₂

H-C(5-NPys)RKFFARIRGGRGU(5-Npys)-NH₂

Refernces

• 1、 Flemer, Stevenson. "A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives". . p. 1257 - 1264. Retrieved 2015/04/14.
• 2、 Schroll, Alayne L.,Hondal, Robert J.,Flemer, Stevenson. "The use of 2,2′-dithiobis(5-nitropyridine) (DTNP) for deprotection and diselenide formation in protected selenocysteine-containing peptides". experimental part. p. 155 - 162. Retrieved 2012/05/20.