143327-78-0

Basic information

• Product Name: Carbamic acid, [(1S)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester
• Synonyms: Carbamic acid, [(1S)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester
• CAS NO: 143327-78-0
• Molecular Formula: C₁₁H₁₉NO₂
• Molecular Weight: 197.27406
• Product Categories: N-BOC
• Mol File: 143327-78-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(1S)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester(143327-78-0)
• EPA Substance Registry System: Carbamic acid, [(1S)-1-(1-methylethyl)-2-propynyl]-, 1,1-dimethylethyl ester(143327-78-0)

Safety Data

• Hazardous Substances Data: 143327-78-0(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 79069-51-5 (S)-N-tert-butoxycarbonylvalinal 
• 87694-52-8 tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 13734-41-3 t-Boc-L-valine 
• 56438-76-7 3-benzoyloxy-4-methyl-pent-1-yne 
• 16169-84-9 (RS)-4-methyl-pent-1-yn-3-acetoxy 
• 565-68-4 4-methylpent-1-yn-3-ol 
• 1310480-48-8 (S)-2-methoxy-N-(4-methylpent-1-yn-3-yl)aniline 
• 293329-55-2 tert-butyl 1-(methoxy(methyl)amino)-3-methyl-1-oxobutan-2-ylcarbamate 
• 176962-19-9 (S)-1-(1'-methyl)-ethyl-3,3-dibromo-N-(t-butoxycarbonyl)-2-propenamine 
• 27491-70-9 dimethyl diazomethylphosphonate 

Downstream Products

• 1198399-51-7 C₁₉H₂₈N₄O₂ 
• 1198399-54-0 C₃₅H₄₆N₁₀O₂ 

Relevant articles and documents

1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics

Peptidotriazolamers are hybrid foldamers combining features of peptides and triazolamers—repetitive peptidomimetic structures with triazoles replacing peptide bonds. We report on the synthesis of a new class of peptidomimetics, containing 1,5-disubstituted 1,2,3-triazoles in an alternating fashion with amide bonds and the analysis of their conformation in solid state and solution. Homo- or heterochiral peptidotriazolamers were obtained from enantiomerically pure propargylamines with stereogenic centers in the propargylic position and α-azido esters by ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC) under microwave conditions in high yields. With such building blocks the peptidotriazolamers are readily available by solution phase synthesis. While the conformation of the homochiral peptidotriazolamer Boc-Ala[5Tz]Phe-Val[5Tz]Ala-Leu[5Tz]Val-OBzl resembles that of a β VIa1 turn, the heterochiral peptidotriazolamer Boc-d-Ala[5Tz]Phe-d-Val[5Tz]Ala-d-Leu[5Tz]Val-OBzl adopts a polyproline-like repetitive structure.

Radiolabeled antagonistic bombesin peptidomimetics for tumor targeting

The replacement of amide bonds in the backbone of peptides by proteolytically stable 1,2,3-triazole isosteres can provide novel peptidomimetics with promising properties for the development of tumor-targeting radiopeptides. On the basis of our previous work with radiolabeled agonistic bombesin (BBN) derivatives of the sequence [Nle14]BBN(7-14), we substituted selected amide bonds of the structurally closely related antagonistic peptide analog JMV594. With the exception of the C-terminal modification, amide-to-triazole substitutions tolerated by [Nle 14]BBN(7-14) without loss of biological function led to abolished receptor affinity in the case of JMV594. These findings provide an additional piece of evidence for the currently disputed differences in the modes of action of agonistic and antagonistic gastrin-releasing peptide receptor (GRPR)-targeting radiopeptides.

Enantioselective copper-catalysed propargylic substitution: Synthetic scope study and application in formal total syntheses of (+)-anisomycin and (-)-cytoxazone

A copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic esters with different side chains (R=Ar, Bn, alkyl) into their amine counterparts in very high yields and with good enantioselectivities (up to 90% enantiomeric excess (ee)). Different amine nucleophiles were applied in the reactions and the highest enantioselectivities were obtained for aniline and its analogues. Interestingly, some carbon nucleophiles could also be used and with indoles excellent ee values were obtained (up to 98% ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)-anisomycin and the cytokine modulator (-)-cytoxazone. Copyright