477191-17-6

Usage

Uses

Used in Pharmaceutical Industry:
Carbamic acid, [(1S)-1-(hydroxymethyl)-2-oxopropyl]-, 1,1-dimethylethyl ester is used as an intermediate in the synthesis of pharmaceuticals for its potential biological activity and therapeutic applications.
Used in Agrochemical Industry:
Carbamic acid, [(1S)-1-(hydroxymethyl)-2-oxopropyl]-, 1,1-dimethylethyl ester is used as a precursor in the development of agrochemicals, contributing to the creation of effective and safe products for agricultural use.

Upstream product

• 75-16-1 methylmagnesium bromide 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 167102-63-8 (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone 

Relevant academic research and scientific papers

An improved method for culturing Streptomyces sahachiroi: Biosynthetic origin of the enol fragment of azinomycin B

Azinomycin B is an environmental DNA crosslinking agent produced by the soil microorganism Streptomyces sahachiroi. While the agent displays potent cytotoxic activities against leukemic cell lines and animal mouse models, the lack of a consistent supply of the natural product has hampered detailed biological investigations on the compound, including its mode of action and biosynthesis. We report here a significant methodological improvement in the culturing of the bacterium, which allows reliable and steady production of the natural product in good yields. The key experimental step involves the culturing of the strain on dehydrated plates, followed by the generation of a two-stage starter culture and subsequent fermentation of the strain under nutrient-starved conditions. We illustrate use of this culture system by investigating the formation of the enol fragment of the molecule in isotopic labeling experiments with threonine and several advanced precursors (β-ketoamino acid 3, β-hydroxyamino aldehyde 4, and β-ketoaminoaldehyde 5). The results unequivocally show that threonine is the most advanced precursor accepted by the NRPS (non-ribosomal peptidyl synthetase) machinery for final processing and construction of the enol moiety of the natural product.

Serine as chiral educt for the practical synthesis of enantiopure N-protected β-hydroxyvaline

N-tert-Butyloxycarbonyl- and N-benzenesulfonyl-β-hydroxyvalines 1a and 1b were, respectively, synthesized in enantiomerically pure form by a two-step protocol from their enantiomeric N-protected serine methyl esters 2a and 2b. The addition of CH3MgBr to 2a and 2b provided diols 3a and 3b, respectively as major products in 83% and 81% yields. Selective oxidation of diols 3a and 3b was performed using a TEMPO, NaClO2, NaOCl cocktail in 96% and 93% respective yields. This two-step process effectively furnished multigram amounts of enantiopure N-Boc-β-hydroxyvaline 1a.