849440-33-1

Basic information

• Product Name: Boc-3,5-Dimethy-L-Phenylalanine
• Synonyms: Boc-3,5-Dimethy-L-Phenylalanine;Boc-Phe(3,5-Me2)-OH;BOC-3,5-DIMETHYL-L-PHENYLALANINE;Boc-Phe(3,5-Me)-OH;(2S)-2-[(TERT-BUTOXY)CARBONYLAMINO]-3-(3,5-DIMETHYLPHENYL)PROPANOIC ACID
• CAS NO: 849440-33-1
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.35812
• Mol File: 849440-33-1.mol

Chemical Properties

• Melting Point: 106-110 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Boiling Point: 452.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.123±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.94±0.10(Predicted)
• CAS DataBase Reference: Boc-3,5-Dimethy-L-Phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-3,5-Dimethy-L-Phenylalanine(849440-33-1)
• EPA Substance Registry System: Boc-3,5-Dimethy-L-Phenylalanine(849440-33-1)

Safety Data

• Hazardous Substances Data: 849440-33-1(Hazardous Substances Data)

Upstream product

• 27129-86-8 1-bromomethyl-3,5-dimethylbenzene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1241680-65-8 3',5'-dimethyl-L-phenylalanine 

Downstream Products

• 943726-71-4 N^α-tert-butyloxycarbonyl-3',5'-dimethyl-L-phenylalanyl-L-phenylalanylamide 
• 943726-78-1 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-3',5'-dimethyl-L-phenylalanyl-L-phenylalanylamide 
• 943726-79-2 N^α-tert-butyloxycarbonyl-2',6'-dimethyl-L-tyrosyl-L-prolyl-3',5'-dimethyl-L-phenylalanyl-L-phenylalanylamide 
• 1229620-64-7 Nα-(tert-butoxycarbonyl)-N-(cyanomethyl)-3,5-dimethyl-L-phenylalaninamide 
• 1352542-97-2 C₃₂H₄₃N₅O₄S₂ 

Relevant articles and documents

CATHEPSIN B INHIBITORS

Compounds of formula I, including individual diastereomers thereof and pharmaceutically acceptable salts and hydrates thereof, are selective inhibitors of cathepsin B, and are useful in treating pathological conditions that are treated by inhibiting cathepsin B.

CATHEPSIN CYSTEINE PROTEASE INHIBITORS FOR THE TREATMENT OF VARIOUS DISEASES

The present invention relates to compounds capable of inhibiting and/or decreasing the activity of one or more cathepsins, thereby treating and/or preventing various disease states associated with one or more cysteine proteases including, but not limited

Bifunctional [2′,6′-dimethyl-L-tyrosine1] endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed μ-agonist/δ-antagonist and dual μ-agonist/δ-agonist opioid ligands

Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) and [Dmt1]EM-2 (Dmt = 2′,6′-dimethyl-L-tyrosine) analogues, containing alkylated Phe3 derivatives, 2′-monomethyl (2, 2′), 3′,5′- and 2′,6′-dimethyl (3, 3′, and 4′, respectively), 2′,4′,6′-trimethyl (6, 6′), 2′-ethyl-6′-methyl (7, 7′), and 2′-isopropyl-6′- methyl (8, 8′) groups or Dmt (5, 5′), had the following characteristics: (i) [Xaa3]EM-2 analogues exhibited improved μ- and δ-opioid receptor affinities. The latter, however, were inconsequential (Kiδ = 491-3451 nM). (ii) [Dmt 1,-Xaa3]EM-2 analogues enhanced μ- and δ-opioid receptor affinities (Kiμ = 0.069-0.32 nM; K iδ = 1.83-99.8 nM) without κ-opioid receptor interaction. (iii) There were elevated μ-bioactivity (IC50 = 0.12-14.4 nM) and abolished δ-agonism (IC50 > 10 μM in 2′, 3′, 4′, 5′, 6′), although 4′ and 6′ demonstrated a potent mixed μ-agonism/δ-antagonism (for 4′, IC50μ = 0.12 and pA2 = 8.15; for 6′, IC50μ = 0.21 nM and pA2 = 9.05) and 7′ was a dual μ-agonist/δ-agonist (IC50 μ = 0.17 nM; IC50δ = 0.51 nM).

Asymmetric synthesis of all six regioisomers of N-boc-dimethylphenylalanines

All possible regioisomers of dimethyl-substituted (S)-phenylalanine were efficiently synthesized by reacting the Ni(II)-complex of the chiral Schiff base of glycine with (S)-2-N-(N-benzylprolyl)-aminobenzophenone.