176504-16-8

Usage

Structure

A derivative of propanol, containing an amino group (-NH2) and a dimethylsilyl group (-Si(CH3)3) attached to the propanol backbone

Chirality

The compound is chiral, with a (2R)-stereoisomer, meaning that it has a specific three-dimensional arrangement of atoms

Uses

Primarily used in organic synthesis and as a reagent in chemical reactions

Applications

Useful in a variety of applications, including pharmaceuticals, biochemistry, and material science

Potential

Has potential as a building block for the development of new chemicals and materials.

Upstream product

• 126027-32-5 O-(tert-butyldimethylsilyl)-L-serine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 98642-61-6 (2S)-2-amino-3-(tert-butyldimethylsilanyloxy)propionic acid methyl ester 

Downstream Products

• 176504-18-0 (R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazole 
• 152491-85-5 (R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Environment-friendly synthesis method of linezolid and intermediate thereof

The invention relates to a more environment-friendly synthesis method of linezolid and a key intermediate thereof. The more environment-friendly synthesis method is characterized in that the key intermediate of linezolid is prepared through the steps of hydroxyl protection, carboxyl reduction, hydroxyl halogenation, ring closing, halogenation after hydroxyl deprotection, ring opening and the likeby taking a natural chiral product L-serine as an initial raw material. According to the more environment-friendly synthesis method provided by the invention, a chiral center is introduced by adoptingthe natural chiral product, the reaction yield is high, the technological operation is simple, the product purity is high, and the synthesis method is more environment-friendly and is suitable for industrial production.

Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides

The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2·DME and a newly developed C2-symmetric oxazoline ligand plays a key role in selective ring opening of seve

Synthesis of an (R)-Garner-type aldehyde from L-serine: Useful building block for a (+)-furanomycin derivative

(+)-Furanomycin is an antibiotic that substitutes for L-isoleucine in bacterial protein translation. We propose here a new short synthesis of a useful intermediate, a 1,2-diprotected 2-aminopent-4-ene-1,3-diol, starting from the inexpensive natural amino acid L-serine, and via a Garner-type aldehyde. The (R)-α-amino aldehyde was obtained by the construction of an oxazoline ring between the N-protected amino group and the hydroxy group that resulted from reduction of the carboxylic acid functionality of L-serine. Georg Thieme Verlag Stuttgart.

A convenient procedure for the reduction of S-(+)-silyl serine methyl ester to chiral serinol derivatives

The reduction of S-(+)-serine methyl ester silyl ether with NaBH4 followed by acidic workup produced the chiral serinol derivatives with minimum racemization. Addition of MeMgBr gave the functionalized amine diol in high yield with no racemization.