154476-57-0

Basic information

• Product Name: 1 3-BIS(TERT-BUTOXYCARBONYL)GUANIDINE
• Synonyms: 1,3-BIS(TERT-BUTOXYCARBONYL)GUANIDINE, 9 8%;N,N'-DI(TERT-BUTOXYCARBONYL)GUANIDINE;1,3-Bis(Tert-butyoxycarbonyl)guanidine;1,3-Bis(tert-butoxycarbonyl)guanidine 98%;N,N'-Bis(tert-butoxycarbonyl)guanidine
• CAS NO: 154476-57-0
• Molecular Formula: C₁₁H₂₁N₃O₄
• Molecular Weight: 259.30214
• Product Categories: Guanidines;Nitrogen Compounds;Organic Building Blocks
• Mol File: 154476-57-0.mol

Chemical Properties

• Melting Point: 141-144 °C(lit.)
• Appearance: /
• Density: 1.13g/cm³
• Refractive Index: 1.485
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 8.24±0.46(Predicted)
• CAS DataBase Reference: 1 3-BIS(TERT-BUTOXYCARBONYL)GUANIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 3-BIS(TERT-BUTOXYCARBONYL)GUANIDINE(154476-57-0)
• EPA Substance Registry System: 1 3-BIS(TERT-BUTOXYCARBONYL)GUANIDINE(154476-57-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 154476-57-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1,3-Bis(tert-butoxycarbonyl)guanidine is used as a key intermediate in the synthesis of (-)-crispine E, a complex organic molecule with potential pharmaceutical applications. Its role in this process is to produce a guanidinyl derivative, which is crucial for the successful completion of the synthesis.
Used in Chemical Research:
In the field of chemical research, 1,3-bis(tert-butoxycarbonyl)guanidine is used as a reagent during the preparation of 1,6-diphenylnaphthalenes. These compounds are of interest due to their unique chemical properties and potential applications in various industries.
Used in the Synthesis of N-Substituted 2-Aminoimidazole Inhibitors:
1,3-Bis(tert-butoxycarbonyl)guanidine is also utilized in the synthesis of N-substituted 2-aminoimidazole inhibitors. These inhibitors have potential applications in the development of new drugs and therapies, particularly in the treatment of various diseases and disorders.
Overall, 1,3-bis(tert-butoxycarbonyl)guanidine is a versatile compound with applications in various industries, including pharmaceuticals, chemical research, and drug development. Its ability to form guanidinyl derivatives and participate in the synthesis of complex organic molecules makes it a valuable asset in these fields.

InChI:InChI=1/C11H21N3O4/c1-10(2,3)17-8(15)13-7(12)14-9(16)18-11(4,5)6/h1-6H3,(H3,12,13,14,15,16)

Upstream product

• 107819-90-9 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea 
• 145013-05-4 tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 867-44-7 S-Methylisothiourea sulfate 
• 322474-21-5 N,N'-bis-Boc-S-methyl-isothiourea 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 870193-64-9 [amino-(3-benzylureido)-methylene]carbamic acid tert-butyl ester 
• 294664-68-9 (2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate 
• 294664-67-8 (2S,2'S,5'R)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate 
• 294664-66-7 (2S,2'S,5'S)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate 
• 1032374-14-3 N,N'-bis-tert-butoxycarbonyl-4'-acetylamino-6-(2-guanidinoethylamino)biphenyl-3-carboxylic acid (4-dibenzylaminophenyl)amide 
• 1032374-44-9 N,N'-bis-tert-butoxycarbonyl-N''-[4-(5-dibenzylamino-1H-indol-2-yl)phenyl]-2-guanidinoacetamide 
• 1032374-29-0 N,N'-bis-tert-butoxycarbonyl-4-(2-guanidinoacetylamino)-3-naphthalen-2-ylbenzoic acid 
• 936571-56-1 4-[2-(N,N'-bis-tert-butoxycarbonylguanidino)-ethylamino]benzoic acid 
• 1187179-34-5 3-[N₁,N₂-bis(t-butyloxycarbonyl)guanidino]-1-(tritylaminooxyacetyl)aminopropane 
• 1243154-05-3 C₂₉H₄₃N₇O₇ 
• 191987-23-2 4-[(N¹,N²-bis(tert-butyloxycarbonyl)guanidino)methyl]benzoic acid 

Relevant articles and documents

RETRACTED ARTICLE: Synthesis and bioevaluation of aryl-guanidino polyamine conjugates targeting the polyamine transporter

Aryl-guanidino polyamine conjugates were prepared to evaluate their recognition for polyamine transporter (PAT) via a-difluoromethylornithine (DFMO) and spermidine (SPD)-treated B16 cell lines. The potent synergistic effects of DFMO on guanidino polyamine conjugates indicated that the presence of DFMO strongly facilitates the transport of conjugates into cells via PAT on cell membrane. The apoptotic mechanisms of triamine conjugates 10 and 1 (with and without guanidine groups) revealed that they induced apoptosis of Hela cells through the mitochondrial pathway associated with lysosomes, while DFMO strongly synergizes the function of 10 without changing the apoptotic route. Taken together, guanidino polyamine conjugates can target PAT for transport as normal polyamine ones, and the presence of guanidine in the polyamine vectors does not seem to alter the cellular targets of the conjugates, which may depend mainly on the pharmacophore.

Tailoring the Physicochemical Properties of Antimicrobial Peptides onto a Thiazole-Based γ-Peptide Foldamer

Antimicrobial peptides (AMPs) are amphipathic molecules displaying broad-spectrum bactericidal activity, providing opportunities to develop a new generation of antibiotics. However, their use is limited either by poor metabolic stability or by high hemolytic activity. We herein addressed the potential of thiazole-based γ-peptide oligomers named ATCs as tunable scaffolds to design polycationic AMP mimetics. Knowing the side chain distribution along the backbone, we rationally designed facially amphiphilic sequences with bactericidal effect in the micromolar range. Since no hemolytic activity was detected up to 100 μM, this class of compounds has shown the potential for therapeutic development.

MODIFIED PEPTIDES AND THEIR USE

The invention relates to a compound of formula (A) wherein n is an integer from 1 to 6, and R1, R1', R2, R2', R3, R3' are cationic or hydrophobic residues.

N,N,N-Tris(tert-butoxycarbonyl)-l-arginine: five isoforms whose obtainment depends on procedure and scrupulous NMR confirmation of their structures

l-arginine is often covalently linked to vectors for gene or drug delivery as a means of increasing their transfection activity and reducing toxicity. This strategy relies on the protection of basic nitrogen atoms, for example, by employing the tert-butoxycarbonyl group. Our aim in the present work was to prepare the widely described αN,ωN,ω′N-tris(tert-butyloxycarbonyl)-l-arginine as a single isomer in high yield and with high levels of purity for use in the esterification of dendrimers with several peripheral hydroxyl groups. Following three reported protocols which assured this goal, we observed the unexpected formation of four additional isomers. Using the first procedure, αN,ωN,ω′N-tris(tert-butyloxycarbonyl)-l-arginine was never obtained. The second procedure delivered the desired compound as a mixture of geometric isomers (E/Z), while the third protocol led to a single isomer in high yield and purity, but with an unreported symmetrical structure. Since Boc protection is transient, this discovery would seem to be of little interest, but preliminary results from an ongoing investigation of the behavior of each of the isomers obtained in the esterification reactions of interest has shown that their reactivity depends on their structure. Although this research is ongoing, here we report a detailed description of these unexpected results, along with an NMR investigation focusing on the double-bond geometry and position which enabled confirmation of the structures.

Stable peptide-based PACE4 inhibitors

It is provided PACE4 inhibitors and their uses for treating infection, cancer. Particularly, it is provided a method or use for the treatment of a cancer in a subject, comprising administering to the subject a therapeutically effective amount of the PACE4 inhibitors or the composition disclosed.

ANTIBACTERIAL THERAPEUTICS AND PROPHYLACTICS

The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.

Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation

The preparation of peptide fragments containing dehydrovaline and dehydroisoleucine moieties present in the antibiotic myxovalargin is reported. Peptide formation is based on a copper-mediated C-N cross-coupling protocol between an acyl amide and a peptidic vinyl iodide. The presence of a neighboring arginine in the vinyl iodide posed a challenge with respect to the choice of the protecting group and the reaction conditions. It was found that ornithine - a suitable precursor - is better suited than arginine for achieving good yields for the C-N cross-coupling reaction. The optimized conditions were utilized for the synthesis of peptides 32, 33, 39 and 40 containing a neighboring ornithine as well as for the tripeptide 44 containing dehydroisoleucine with the correct stereochemistry.

LYSINE OLIGOMER DERIVATIVE AND CARTILAGE TISSUE MARKER MADE THEREOF

There is provided a lysine oligomer derivative, wherein an ε-amino group and a carboxyl group of lysines are linked via a peptide bond, and a group capable of generating or absorbing electromagnetic wave is bonded to a C-terminal carboxyl group, an N-terminal amino group and/or an α-amino group. This lysine oligomer derivative has the characteristic of specifically accumulating in the cartilage matrix and can generate or absorb an electromagnetic wave, and is, therefore, useful as a cartilage tissue marker.

Enantioselective diamination with novel chiral hypervalent iodine catalysts

Vicinal diamines constitute one the most important functional motif in organic chemistry because of its wide occurrence in a variety of biological and pharmaceutical molecules. We report an efficient metal-free, highly stereoselective intramolecular diamination using a novel chiral hypervalent iodine reagent together with its application as an efficient catalyst for the synthesis of diamines.

Improved synthesis of no-carrier-added [*I]MIBG and its precursor

3-(Trimethylstannyl)benzyl alcohol was coupled in a Mitsunobu reaction with bis(Boc)-guanidine to give bis(Boc)-protected 3-(trimethylstannyl) benzylguanidine used as precursor for [*I]MIBG. Radioiodination with [131I]iodine generated from [131I]NaI and chloramine-T, removal of Boc groups, and purification by HPLC gave no-carrier-added tracer [*I]MIBG (81% radiochemical yield, 99% chemical purity) used for imaging tumors of neuroendocrine origin. The structures of bis(Boc)-guanidine and bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine were secured by single crystal X-ray structure analyses.