192764-16-2

Upstream product

• 192764-08-2 N-benzyl-N-[(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)ethyl]hydroxylamine 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 61821-86-1 (R)-2,2-dimethyl-1,3-dioxolan-4-yl methyl ketone 
• 100-46-9 benzylamine 
• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 75-16-1 methylmagnesium bromide 
• 917-54-4 methyllithium 
• 180839-79-6 (S)-N-(1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethylidene)-1-phenylmethanamine 

Downstream Products

• 192764-27-5 (2S,3R)-3-Benzylamino-1-(tert-butyl-dimethyl-silanyloxy)-butan-2-ol 
• 192764-22-0 (2S,3R)-3-Benzylamino-butane-1,2-diol 

Relevant academic research and scientific papers

Diastereoselective reduction of ketimines derived from (R)-3,4-dihydroxybutan-2-one: an alternative route to key intermediates for the synthesis of anticancer agent ES-285

A simple and convenient procedure for the diastereoselective reduction of imines derived from (R)-3,4-dihydroxybutan-2-one is described. The use of sodium borohydride as a reducing agent in the reactions with pre-synthesised imines gave aminodiol derivatives with the appropriate stereochemistry for use as intermediates in the synthesis of anticancer agent ES-285. The aminodiols were isolated in ca. 62% yield.

NOVEL COMPOUND 395

A compound of formula (1) and pharmaceutically acceptable salts thereof for use in the treatment of chemokine mediated diseases and conditions.

Asymmetric synthesis of ES-285, an anticancer agent isolated from marine sources

The asymmetric synthesis of (2S,3R)-2-amino-3-octane-decanol hydrochloride (ES-285-HC1) was achieved in eight steps in ca. 38% overall yield from the N-benzylimine-derived from. (R)-2,3-O-isopropylidene glyceraldehyde, which is easily available on gram sc

Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2- O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and α- hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.

Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

The stereoselective addition of Grignard reagents to α-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols.