16881-34-8

Basic information

• Product Name: N-benzyloxycarbonyl-L-phenylalanine t-butyl ester
• CAS NO: 16881-34-8
• Molecular Weight: 355.434
• Mol File: 16881-34-8.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: N-benzyloxycarbonyl-L-phenylalanine t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyloxycarbonyl-L-phenylalanine t-butyl ester(16881-34-8)
• EPA Substance Registry System: N-benzyloxycarbonyl-L-phenylalanine t-butyl ester(16881-34-8)

Safety Data

• Hazardous Substances Data: 16881-34-8(Hazardous Substances Data)

Upstream product

• 3588-57-6 Z-DL-Phe-OH 
• 75-65-0 tert-butyl alcohol 
• 6645-42-7 N-benzyloxycarbonyl-DL-phenylalanine-(N'-phenyl-hydrazide) 
• 1907-33-1 lithium tert-butoxide 
• 558-17-8 tert-Butyl iodide 
• 19506-72-0 benzyl-8-quinolyl carbonate 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 118786-34-8 1,1-dimethylethyl 2-[[(phenylmethoxy)carbonyl]amino]-2-propenoate 
• 98-80-6 phenylboronic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1161-13-3 N-Cbz-L-Phe 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 501-53-1 benzyl chloroformate 
• 63-91-2 L-phenylalanine 

Downstream Products

• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 60379-01-3 N-(benzyloxycarbonyl)-L-phenylalanine benzyl ester 
• 1361051-52-6 Z-Sar-L-Phe-O(t-Bu) 
• 1246175-34-7 H-Sar-L-Phe-O(t-Bu)*HCl 
• 1313619-01-0 C₃₇H₅₅N₅O₉S 
• 1313618-97-1 C₃₇H₅₅N₅O₉S 
• 1313618-95-9 C₃₈H₅₇N₅O₉S 
• 1313619-20-3 C₂₈H₃₇N₅O₆S 
• 1313619-18-9 C₂₉H₃₉N₅O₆S 
• 1313619-16-7 C₂₈H₃₇N₅O₆S 
• 1313619-14-5 C₂₉H₃₉N₅O₆S 
• 1353757-53-5 (S,E)-tert-butyl 2-benzyl-2-(pyrrolidin-1-yl)-4-(p-toluenesulfonyl)but-3-enoate 
• 1353757-68-2 (S)-tert-butyl 3-phenyl-2-(pyrrolidin-1-yl)propanoate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 

Relevant articles and documents

Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.

4-Biphenylalanine- and 3-Phenyltyrosine-Derived Hydroxamic Acids as Inhibitors of the JumonjiC-Domain-Containing Histone Demethylase KDM4A

Overexpression of the histone lysine demethylase KDM4A, which regulates H3K9 and H3K36 methylation states, has been related to the pathology of several human cancers. We found that a previously reported hydroxamate-based histone deacetylase (HDAC) inhibitor (SW55) was also able to weakly inhibit this demethylase with an IC50value of 25.4 μm. Herein we report the synthesis and biochemical evaluations, with two orthogonal in vitro assays, of a series of derivatives of this lead structure. With extensive chemical modifications on the lead structure, also by exploiting the versatility of the radical arylation with aryldiazonium salts, we were able to increase the potency of the derivatives against KDM4A to the low-micromolar range and, more importantly, to obtain demethylase selectivity with respect to HDACs. Cell-permeable derivatives clearly showed a demethylase-inhibition-dependent antiproliferative effect against HL-60 human promyelocytic leukemia cells.

Solventless mechanosynthesis of N-protected amino esters

Mechanochemical derivatizations of N- or C-protected amino acids were performed in a ball mill under solvent-free conditions. A vibrational ball mill was used for the preparation of N-protected α- and β-amino esters starting from the corresponding N-unmasked precursors via a carbamoylation reaction in the presence of di-tert-butyl dicarbonate (Boc2O), benzyl chloroformate (Z-Cl) or 9-fluorenylmethoxycarbonyl chloroformate (Fmoc-Cl). A planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.