116300-00-6

Basic information

• Product Name: (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE
• Synonyms: (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-LEUCINYL-DIAZOMETHANE;BOC-L-LEU-CHN2
• CAS NO: 116300-00-6
• Molecular Formula: C₁₂H₂₁N₃O₃
• Molecular Weight: 255.31
• Mol File: 116300-00-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE(116300-00-6)
• EPA Substance Registry System: (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE(116300-00-6)

Safety Data

• Hazardous Substances Data: 116300-00-6(Hazardous Substances Data)

Usage

Description

(S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is a diazo ketone chemical compound that features a BOC-protected amino group and a methyl substituent at the 5-position of the hexanone ring. It is part of the diazo compounds class and is known for its versatility in chemical synthesis.

Uses

Used in Organic Synthesis:
(S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is used as a reagent for the introduction of the diazo group into various organic molecules. The BOC protecting group allows for selective reactions at other functional groups in the molecule, enhancing the compound's utility in organic synthesis.
Used in Cyclopropanation Reactions:
In the chemical industry, (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is used as a reactant in cyclopropanation reactions, which are important for the formation of cyclopropane rings in organic molecules.
Used in Aziridination Reactions:
(S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is also utilized in aziridination reactions, where it helps in the formation of aziridines, which are valuable intermediates in the synthesis of various pharmaceuticals and agrochemicals.
Used in Carbene Transfer Reactions:
Furthermore, (S)-3-BOC-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is employed in carbene transfer reactions, which are crucial for the synthesis of complex organic molecules and have applications in material science and pharmaceuticals.

Upstream product

• 186581-53-3 diazomethane 
• 16937-99-8 N-Boc-D-Leu 

Downstream Products

• 504412-86-6 (Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester 
• 504412-16-2 (S)-2-{(4R,7S)-7-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentyl]-2,2-dimethyl-4,7-dihydro-[1,3,2]dioxasilepin-4-yl}-thiopropionic acid S-benzyl ester 

Relevant articles and documents

Extensively stereodiversified scaffolds for use in diversity-oriented library synthesis

Figure presented The syntheses of stereodiverse libraries of 12 and 19 are reported, where each asterisk represents an independently varied stereocenter. These scaffolds provide additional templates for investigations of geometric diversity in library syn

Design of novel inhibitors of aminopeptidases. Synthesis of peptide-derived diamino thiols and sulfur replacement analogues of bestatin

Investigations were directed toward inhibition of an aminopeptidase, isolated from rat brain, which has been implicated in the metabolic inactivation of enkephalins. The design rationale and synthesis of novel peptidyl diamino thiol inhibitors of rat brain aminopeptidase are presented, along with accompanying structure-activity analysis. Some of the reported compounds are highly active aminopeptidase inhibitors and possess enzyme inhibitory potency in the nanomolar range (62; I50 = 1 nM). Analysis of the data permits speculations on possible modes of binding of diamino thiols to aminopeptidase. Other investigations were directed toward understanding the mode of enzyme binding of the naturally occurring aminopeptidase inhibitor bestatin. On the basis of published models of enzyme binding, replacement of the C-2 hydroxyl group of bestatin by a sulfhydryl group was anticipated to lead to enhanced inhibition due to a strengthened interaction of this group with enzymic zinc. Contrary to expectations, 'thiobestatin' inhibited rat brain aminopeptidase with only the same degree of effectiveness as the corresponding alcohol. Speculations on the possible mode of enzyme-inhibitor binding of bestatin are offered.