450371-16-1

Basic information

• Product Name: {(S)-1-[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• Synonyms: {(S)-1-[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• CAS NO: 450371-16-1
• Molecular Weight: 572.861
• Mol File: 450371-16-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: {(S)-1-[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: {(S)-1-[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester(450371-16-1)
• EPA Substance Registry System: {(S)-1-[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester(450371-16-1)

Safety Data

• Hazardous Substances Data: 450371-16-1(Hazardous Substances Data)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 204577-67-3 (1R)-2-endo-acetyl-2-exo-(trimethylsilyloxy)-1,7,7-trimethylbicyclo[2.2.1]heptane 
• 204577-66-2 1-(2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-endo-2-yl)ethanone 
• 1075216-42-0 2-ethinyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 
• 271600-09-0 [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester 

Downstream Products

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 450371-20-7 [(S)-1-((S)-1-{[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-methyl}-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 450371-18-3 (S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-pentanoic acid 

Relevant articles and documents

Design and synthesis of a novel class of sugar-peptide hybrids: C-linked glyco β-amino acids through a stereoselective "acetate" Mannich reaction as the key strategic element

A new type of sugar-amino acid hybrid, which is comprised of a sugar unit (gluco-, galacto-, or mannopyranose) linked through a C-glycosidic linkage to the β-position of an α-unsubstituted β-amino acid unit, is presented. It is hypothesized that these new compounds, or the oligomeric peptides derived therefrom, might possess the structural features of β-amino acid oligomers and the chemical and enzymatic resistance of C-glycosides to hydrolysis. The synthetic strategy is based on a new Mannich-type reaction between a chiral acetate enolate equivalent and α-amido sulfones derived from the corresponding sugar-C-glycoside aldehydes. While the sugar-C-glycoside aldehyde partner is prepared from well-established transformations on known sugar precursors, the lithium enolate derived from (1 R)-endo-2-acetylisoborneol 3 is employed as the key element. This Mannich approach proceeds with essentially perfect diasteromeric control leading to the new β-amino carbonyl adducts in good yields. Further, cleavage of the camphor auxiliary is smoothly performed by oxidative treatment with ammonium cerium nitrate (CAN). Complementarily, direct peptide-type coupling of the β-amino carbonyl Mannich adducts with an α- or β-amino acid residue and subsequent CAN-promoted detachment of the auxiliary yields dipeptide fragments bearing a sugar-containing aliphatic side chain and is a process that can be iterated. A preliminary conformational study based on the combination of experimental NMR data and molecular mechanics and molecular dynamics (MD) of one particular adduct is also provided.