641617-22-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol is used as a chiral building block for the synthesis of chiral drugs and bioactive compounds. Its application is crucial in the development of pharmaceutical intermediates, including natural products, which often possess unique biological activities and therapeutic properties.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (R)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol is used as a chiral auxiliary. This role is essential for the creation of enantiomerically pure compounds, which are vital in the pharmaceutical industry as the different enantiomers of a drug can have significantly different biological activities and effects.
Used in Asymmetric Catalysis:
(R)-Boc-phenylglycinol is also employed as a ligand in asymmetric catalysis. This application is important for enhancing the selectivity and efficiency of catalytic reactions, leading to the production of enantiomerically pure compounds with fewer side products and higher yields.

Upstream product

• 66211-46-9 (R)-3-amino-1,2-propanediol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1000855-32-2 (R)-3-[N-(benzyloxycarbonyl)amino]-2-hydroxypropanal 
• 97859-49-9 (R)-5-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 641617-09-6 (2R/S,4R)-4-[(N-benzyloxycarbonyl)aminomethyl]-1,3,2λ4-dioxathiolane-2-one 

Relevant academic research and scientific papers

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidases SpsB and/or LepB, an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

Modular, gold-catalyzed approach to the synthesis of lead-like piperazine scaffolds

Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

D-fructose-6-phosphate aldolase-catalyzed one-pot synthesis of iminocyclitols

A one-pot chemoenzymatic method for the synthesis of a variety of new iminocyclitols from readily available, non-phosphorylated donor substrates has been developed. The method utilizes the recently discovered fructose-6-phosphate aldolase (FSA), which is functionally distinct from known aldolases in its tolerance of different donor substrates as well as acceptor substrates. Kinetic studies were performed with dihydroxyacetone (DHA), the presumed endogenous substrate for FSA, as well as hydroxy acetone (HA) and 1-hydroxy-2-butanone (HB) as donor substrates, in each case using glyceraldehyde-3-phosphate as acceptor substrate. Remarkably, FSA used the three donor substrates with equal efficiency, with kcat/KM-values of 33, 75, and 20 M -1 s-1, respectively. This level of donor substrate tolerance is unprecedented for an aldolase. Furthermore, DHA, HA, and HB were accepted as donors in FSA-catalyzed aldol reactions with a variety of azido- and Cbz-amino aldehyde acceptors. The broad substrate tolerance of FSA and the ability to circumvent the need for phosphorylated substrates allowed for one-pot synthesis of a number of known and novel iminocyclitols in good yields, and in a very concise fashion. New iminocyclitols were assayed as inhibitors against a panel of glycosidases. Compounds 15 and 16 were specific α-mannosidase inhibitors, and 24 and 26 were potent and selective inhibitors of β-N-acetylglucosaminidases in the submicromolar range. Facile access to these compounds makes them attractive core structures for further inhibitor optimization.