(S,E)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid

Base Information

• Chemical Name: (S,E)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid
• CAS No.: 97745-69-2
• Molecular Formula: C₂₁H₃₈N₄O₈
• Molecular Weight: 474.555
• DSSTox Substance ID: DTXSID30464257
• Nikkaji Number: J1.996.460D
• Mol file: 97745-69-2.mol

Synonyms:108787-91-3;(S,E)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-5-((2,2,10,10-tetramethyl-4,8-dioxo-3,9-dioxa-5,7-diazaundecan-6-ylidene)amino)pentanoic acid;(2S)-5-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;885110-90-7;Boc-L-Arg(Boc)2-OH;Boc-Arg(Boc)2-OH (symmetrical);Boc-Arg-(Boc)2-OH;SCHEMBL3439703;SCHEMBL22473734;SCHEMBL25245536;DTXSID30464257;BGOFOVHACSQSIE-ZDUSSCGKSA-N;MFCD00236819;AKOS016008640;BP-10772;BS-44572;CS-0043322;E77237;N alpha ,N omega ,N omega '-Tris-Boc-L-arginine;(Tert-Butoxy)Carbonyl Arg(Boc)2-OH (Symmetrical);(2S)-5-({bis[(tert-butoxycarbonyl)amino]methylidene}amino)-2-[(tert-butoxycarbonyl)amino]pentanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-5-((2,2,10,10-tetramethyl-4,8-dioxo-3,9-dioxa-5,7-diazaundecan-6-ylidene)amino)pentanoicacid;(S,Z)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid;11-Oxa-2,4,9-triazatridecanoicacid,8-carboxy-4-[(1,1-dimethylethoxy)carbonyl]-3-imino-12,12-dimethyl-10-oxo-,1-(1,1-dimethylethyl)ester,(8S)-;2169299-66-3

Chemical Property of (S,E)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid

Chemical Property:

• PKA: 3.96±0.21(Predicted)
• PSA: 164.65000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 4.32260
• Storage Temp.: -15°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 474.26896418
• Heavy Atom Count: 33
• Complexity: 698

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-5-(1,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCCN=C(NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCCN=C(NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)C(=O)O

Technology Process of (S,E)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid

There total 1 articles about (S,E)-5-(2,3-Bis(tert-butoxycarbonyl)guanidino)-2-((tert-butoxycarbonyl)amino)pentanoic acid 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: 26.0%

di-tert-butyl dicarbonate (24424-99-5) + t-butyloxycarbonyl-L-arginine (13726-76-6,78603-12-0) → αN,ωN-bis(tertbutoxycarbonyl)-L-arginine (17907-22-1) + αN,ωN,ω'N-tris(tert-butoxycarbonyl)-L-arginine + N2,N5-bis(tert-butoxycarbonyl)-N5-{[(tert-butoxycarbonyl)amino](imino)methyl}-L-ornithine (108787-89-9,108787-90-2,97745-69-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 - 20 ℃; for 42h;

DOI:10.1007/s11164-017-3199-6

Reference yield:

2-{4-[2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyanopyridin-4-yl]phenoxy}ethyl L-valinate trifluoroacetate (1110660-30-4) + N2,N5-bis(tert-butoxycarbonyl)-N5-{[(tert-butoxycarbonyl)amino](imino)methyl}-L-ornithine (108787-89-9,108787-90-2,97745-69-2) → C51H63ClN10O10S2

Guidance literature:

N²,N⁵-bis(tert-butoxycarbonyl)-N⁵-{[(tert-butoxycarbonyl)amino](imino)methyl}-L-ornithine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 0.5h;

2-{4-[2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyanopyridin-4-yl]phenoxy}ethyl L-valinate trifluoroacetate; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

N2,N5-bis(tert-butoxycarbonyl)-N5-{[(tert-butoxycarbonyl)amino](imino)methyl}-L-ornithine (108787-89-9,108787-90-2,97745-69-2) → H2N-tyrosyl-N,N'-di-Boc-spermine-α-NG,G'-tri-Boc-L-arginine di-amide (144117-64-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / DCC / ethyl acetate / 1 h / Ambient temperature

2: 90 percent / dimethylformamide / 12 h / Ambient temperature

3: 81 percent / CH₂Cl₂ / 12 h / Ambient temperature

4: 67 percent / H₂ / 10percent Pd-C / methanol / 4 h / 760 Torr / Ambient temperature

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)81575-1

upstream raw materials:

di-tert-butyl dicarbonate

t-butyloxycarbonyl-L-arginine

Downstream raw materials:

6-carbobenzoxyaminocaproic-N⁵,N¹⁰-di-tert-butoxycarbonyl-spermine-N^α,N^δ,N^ω-tri-tert-butoxycarbonyl-L-arginine amide

N-<6-(p-azidobenzamide)-caproyl>-tyrosyl-N,N'-di-Boc-spermine-N-α-N^G,N^G'-tri-Boc-L-arginine-di-amide

N-Cbz-tyrosyl-spermine-N-α-N^G,^G'-tri-Boc-L-arginine di-amide

H2N-tyrosyl-N,N'-di-Boc-spermine-α-N^G,^G'-tri-Boc-L-arginine di-amide

Refernces