115313-19-4

Basic information

• Product Name: (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE
• Synonyms: N-ALPHA-TERT-BUTYLOXYCARBONYL-L-PHENYLALANINYL-DIAZOMETHANE;(S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE;N-alpha-t-Butyloxycarbonyl-L-phenylalaninyl-diazomethane, (S)-3-Boc-amino-1-diazo-3-phenyl-2-butanone
• CAS NO: 115313-19-4
• Molecular Formula: C₁₅H₁₉N₃O₃
• Molecular Weight: 289.33
• Mol File: 115313-19-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE(115313-19-4)
• EPA Substance Registry System: (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE(115313-19-4)

Safety Data

• Hazardous Substances Data: 115313-19-4(Hazardous Substances Data)

Usage

Description

(S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE is a chemical compound with the molecular formula C17H21N3O3. It is a diazo compound, which means it contains a nitrogen-nitrogen double bond. (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE features a butanone backbone with a phenyl group and an amino group, both of which are protected with a BOC (tert-butyloxycarbonyl) group. The BOC group can be removed under specific conditions, allowing the compound to participate in chemical reactions. Its properties and potential uses make it a valuable tool for the preparation of various organic molecules in laboratory settings.

Uses

Used in Organic Synthesis:
(S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE is used as a reagent for the formation of new carbon-carbon bonds in organic synthesis. Its diazo compound nature allows for unique reactions and bond formations that can be beneficial in creating complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE can be used as a key intermediate in the development of new drugs. Its ability to form carbon-carbon bonds and the presence of a protected amino group make it a versatile building block for medicinal chemists.
Used in Material Science:
(S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE may also find applications in material science, where its unique structure and reactivity can be utilized to create novel materials with specific properties, such as improved strength or chemical resistance.
Used in Chemical Research:
As a diazo compound with a protected amino group, (S)-3-BOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE can be employed in academic and industrial research to explore new reaction pathways, develop innovative synthetic methods, and understand the fundamental chemistry of diazo compounds.

Upstream product

• 186581-53-3 diazomethane 
• 60398-40-5 C₉H₁₁NO₂C₅H₈O₂CO₂C₄H₈ 
• 18942-49-9 Boc-D-Phe-OH 

Downstream Products

• 150935-37-8 (R)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid t-butyl ester 
• 101555-61-7 (R)-3-t-butoxycarbonylamino-4-phenylbutyric acid 
• 115313-20-7 methyl 3-(R)-[N-(tert-butoxycarbonyl)amino]-4-phenylbutanoate 
• 115364-68-6 (R)-N-<2-(benzyloxacarbonyl)-1-oxoethyl>-3-amino-4-phenyl-N'-(benzyloxy)butanamide 
• 115364-65-3 (R)-N-tert-butyloxycarbonyl-3-amino-4-phenyl-N'-(benzyloxy)butanamide 
• 115364-69-7 (R)-N-(2-carboxy-1-oxoethyl)-3-amino-4-phenyl-N'-hydroxybutanamide 
• 115364-67-5 (R)-3-amino-4-phenyl-N'-(benzyloxy)butanamide trifluoroacetate 
• 115364-79-9 (R)-3-amino-4-phenyl-N'-(benzyloxy)-N'-methylbutanamide trifluoroacetate 
• 115364-80-2 (R)-N-<2-(benzyloxacarbonyl)-1-oxoethyl>-3-amino-4-phenyl-N'-(benzyloxy)-N'-methylbutanamide 
• 115364-77-7 (R)-N-tert-butyloxycarbonyl-3-amino-4-phenyl-N'-(benzyloxy)-N'-methylbutanamide 
• 115364-81-3 (R)-N-(2-carboxy-1-oxoethyl)-3-amino-4-phenyl-N'-hydroxy-N'-methylbutanamide 

Relevant articles and documents

TAPP analogs containing β3-homo-amino acids: Synthesis and receptor binding

β-Amino acids containing α,β-hybrid peptides show great potential as peptidomimetics. In this paper, we describe the synthesis and affinity to μ-opioid and δ-opioid receptors of α,β-hybrids, analogs of the tetrapeptide Tyr- d-Ala-Phe-Phe-NH2 (TAPP). Each amino acid was replaced with an l- or d-β3-h-amino acid. All α,β-hybrids of TAPP analogs were synthesized in solution and tested for affinity to μ-opioid and δ-opioid receptors. The analog Tyr-β3h- d-Ala-Phe-PheNH2 was found to be as active as the native tetrapeptide.

Aminodiol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR

A series of HIV protease inhibitors containing a novel C2 symmetrical "aminodiol" core structure were prepared from amino acid starting materials.The ability of the aminodiols to inhibit HIV replication in cell culture is comparable to their ability to inhibit the isolated enzyme, a result compatible with good cell membrane penetration by this class of compounds.Optimization of the structure-activity in this series led to aminodiol 9a (Ki = 100 nM; ED50(HIV-1) = 80 nM) containing P1/P1' benzyl and P2/P2' Boc substituents.Compound 9a is a selective inhibito r of HIV protease versus other aspartyl proteases such as human renin, human cathepsin D, and porcine pepsin.In addition, 9a is equipotent against HIV-1 and HIV-2 in cell culture and demonstrates similar activity in infected T-lymphocytes and PBMCs.After iv and oral administration in rats, 9a displayed significant oral bioavailability (ca. 40percent) and a promising plasma elimination half-life (4 h).