78981-25-6

Basic information

• Product Name: BOC-D-ALA-NH2
• Synonyms: (R)-tert-Butyl (1-amino-1-oxopropan-2-yl)carbamate;N-tert-Butoxycarbonyl-D-alanine amide;N-(tert-Butoxycarbonyl)-D-alaninamideButoxycarbonyl-D-alanine amide;(Tert-Butoxy)Carbonyl D-Ala-NH2;N-(tert-Butoxycarbonyl)-D-alaninamide
• CAS NO: 78981-25-6
• Molecular Formula: C₈H₁₆N₂O₃
• Molecular Weight: 188.225
• Mol File: 78981-25-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 120-121 °C
• Boiling Point: 343.1±25.0 °C(Predicted)
• Appearance: /
• Density: 1.081±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 11.38±0.46(Predicted)
• CAS DataBase Reference: BOC-D-ALA-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-ALA-NH2(78981-25-6)
• EPA Substance Registry System: BOC-D-ALA-NH2(78981-25-6)

Safety Data

• Hazardous Substances Data: 78981-25-6(Hazardous Substances Data)

Usage

General Description

BOC-D-ALA-NH2 is a chemical compound that consists of a BOC (tert-butyloxycarbonyl) protecting group, a D-alanine amino acid, and an amine functional group. It is commonly used in peptide synthesis and as a precursor for the production of other peptides and amino acid derivatives. The BOC protecting group is a commonly used chemical modification that helps to protect the amine group of the D-alanine amino acid during chemical reactions, allowing for controlled and selective modification of the molecule. BOC-D-ALA-NH2 is also used as a building block in the synthesis of complex peptides and can be incorporated into larger peptide chains with other amino acids to create custom-designed peptides for research and pharmaceutical applications.

Upstream product

• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 100927-09-1 (R)-tert-butyl (1-cyanoethyl)carbamate 
• 1051922-87-2 C₁₆H₂₆N₂O₅ 
• 1357830-46-6 tert-butyl 1-(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate 
• 71810-97-4 D-alaninamide hydrochloride 
• 1217317-62-8 (S)-benzyl tert-butyl propane-1,2-diyldicarbamate 
• 33208-99-0 (S)-alaninamide hydrochloride 
• 149632-73-5 dl-1-amino-2-(1,1-dimethylethoxy)carbonylamino-propane 
• 1418192-71-8 C₄₂H₆₅N₅O₁₀S 
• 1418192-73-0 C₄₆H₆₅N₅O₁₀S 
• 35320-22-0 D-alaninamide 
• 1354939-21-1 C₃₇H₆₀N₄O₉Si₂ 
• 1354939-20-0 C₃₇H₆₀N₄O₉Si₂ 
• 1332873-13-8 benzyl 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylate 
• 1262796-98-4 (R)-tert-butyl 1-(3-((4-chlorophenyl)carbamoyl)pyridin-2-ylamino)-1-oxopropan-2-ylcarbamate 

Relevant articles and documents

Solid-Phase Total Synthesis of Yaku'amide B Enabled by Traceless Staudinger Ligation

We report a solid-phase strategy for total synthesis of the peptidic natural product yaku'amide B (1), which exhibits antiproliferative activity against various cancer cells. Its linear tridecapeptide sequence bears four β,β-dialkylated α,β-dehydroamino acid residues and is capped with an N-terminal acyl group (NTA) and a C-terminal amine (CTA). To realize the Fmoc-based solid-phase synthesis of this complex structure, we developed new methods for enamide formation, enamide deprotection, and C-terminal modification. First, traceless Staudinger ligation enabled enamide formation between sterically encumbered alkenyl azides and newly designed phosphinophenol esters. Second, application of Eu(OTf)3 led to chemoselective removal of the enamide Boc groups without detaching the resin linker. Finally, resin-cleavage and C-terminus modification were simultaneously achieved with an ester–amide exchange reaction using CTA and AlMe3 to deliver 1 in 9.1 % overall yield (24 steps from the resin).