188802-16-6

Usage

Physical state

Colorless, flammable liquid

Odor

Strong

Common uses

Solvent, production of pharmaceuticals, cosmetics, and personal care products

Contains a chiral center

Yes, resulting in two possible enantiomers with different chemical and biological properties

Primary use

Pharmaceutical industry for the production of various drugs and biologically active molecules

Utilization

Reagent in organic synthesis

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-44-7 benzyl chloride 
• 1346653-44-8 C₃₀H₃₉NO₃Si 
• 943437-50-1 benzyl (2R)-2-(dibenzylamino)-3-hydroxypropanoate 
• 100-39-0 benzyl bromide 
• 188802-06-4 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionic acid methyl ester 
• 202478-34-0 (R)-methyl 2-(dibenzylamino)-3-hydroxypropanoate 

Downstream Products

• 1647153-55-6 (4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 
• 1647153-54-5 (2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol 
• 1647153-46-5 (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol 
• 188840-00-8 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde 

Relevant academic research and scientific papers

Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds.

A highly stereoselective synthesis of (2S,3S)-β-hydroxyleucine

A highly diastereoselective nucleophilic addition of Grignard reagent to N,N-dibenzyl-O-TBS-serinal 3 was the key step in the present synthesis of (2S,3S)-β-hydroxyleucine 1.