144542-72-3

Usage

Uses

Used in Pharmaceutical Industry:
(3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester is used as a reactant for the preparation of collagen cross-link pyridinolines. Its application in this context is due to its ability to enhance the stability and strength of collagen fibers, which are essential components of connective tissues in the human body. This enhancement can be particularly beneficial in the development of treatments for conditions that involve the degradation or weakening of collagen, such as various forms of arthritis or skin disorders.
Used in Chemical Synthesis:
As a complex organic molecule, (3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-Morpholinecarboxylic Acid tert-Butyl Ester can also be used as an intermediate in the synthesis of other compounds with potential applications in various industries. Its unique structure and functional groups make it a valuable building block for the development of new pharmaceuticals, materials, or specialty chemicals.

Upstream product

• 7766-51-0 4-iodobut-1-ene 
• 112741-49-8 tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate 

Downstream Products

• 937183-38-5 tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate 
• 144607-16-9 C₄₈H₄₈N₂O₈ 
• 174579-93-2 C₄₅H₄₈N₂O₈ 
• 174690-80-3 C₄₅H₄₈N₂O₈ 
• 753010-16-1 tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 
• 753010-17-2 tert-butyl (3S,5S,6R)-3-[(3S)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 
• 753010-18-3 tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 
• 753010-19-4 tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 
• 93923-90-1 (2S,5R)-5-hydroxylysine monohydrochloride 
• 108691-35-6 (2S,5S)-5-hydroxylysine hydrochloride 
• 144542-73-4 (3S,5S,6R)-4-(tert-butoxycarbonyl)-5,6-diphenyl-3-(2'-carbonylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 

Relevant academic research and scientific papers

Total Synthesis of the Bacterial Diisonitrile Chalkophore SF2768

Chalkophores are bacterial natural products that chelate and transport extracellular copper. The diisonitrile natural product SF2768 was first isolated from a Streptomyces species as an antifungal antibiotic and has more recently been characterized as a bacterial chalkophore and potential virulence factor. Herein, we report a modular synthesis of SF2768 and related acyclic analogues, allowing assignment of syn-stereochemistry across the central lactol ring. The copper-binding properties of these diisonitriles have also been studied.

A practical and simple synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine and of a related α-amino acid required for the synthesis of the collagen cross-link pyridinoline

A four step synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine using Williams' glycine template methodology for controlling the stereogenicity at the α-position is reported. This route offers the possibility for the synthesis of all possible isomers of 5-hydroxylysine and of an important α-amino acidic iodohydrin required for the construction of the hydroxylated side chain of the collagen cross-link pyridinoline.

Asymmetric syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids. Studies directed to the design of novel substrate-based inhibitors of L,L-diaminopimelate epimerase

The asymmetric syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids (7a-c) is described. The synthesis features phosphonate coupling of 13 and 14 to form the corresponding E-olefins which are subsequently cyclopropanated and deprotected under dissolving metal conditions.

Asymmetric Synthesis of 2,6-Diaminopimelic Acids

The preparations of (R,R)-2,6-diaminopimelic acid, (S,S)-2,6-diaminopimelic acid, (S,R)-2,6-diaminopimelic acid, and (S,S)-2,7-diaminosuberic acid are described.The synthesis of mono-N-protected (S,R)-2,6-diaminopimelic acid is also described.