3182-94-3

Upstream product

• 64-17-5 ethanol 
• 80-68-2 DL-threonine 
• 5408-04-8 ethyl 2-hydroxyimino-3-oxobutanoate 
• 119645-90-8 (2R^*, 3S^*) ethyl 2-(phenylazo)-3-trimethylsilyloxy-butanoate 
• 119645-91-9 (2R^*, 3S^*) ethyl 2-(phenylhydrazino)-3-trimethylsilyloxy-butanoate 
• 72-19-5 L-threonine 
• 78605-23-9 ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate 
• 75-07-0 acetaldehyde 
• 119645-92-0 3-hydroxy-2-(2-phenylhydrazino)butanoate 

Downstream Products

• 78464-28-5 2-((E)-2-Benzyloxycarbonylamino-3-phenyl-acryloylamino)-3-hydroxy-butyric acid ethyl ester 
• 78464-25-2 2-((E)-2-Benzyloxycarbonylamino-pent-2-enoylamino)-3-hydroxy-butyric acid ethyl ester 
• 78464-26-3 2-((E)-2-Benzyloxycarbonylamino-hex-2-enoylamino)-3-hydroxy-butyric acid ethyl ester 
• 44520-55-0 D-threoninol 
• 109440-65-5 N-thiobenzoyl-DL-allothreonine ethyl ester 

Relevant academic research and scientific papers

Efficient preparation of biologically important 1,2-amino alcohols

An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH 3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60C to yield biologically important 1,2-amino alcohols.

Total synthesis of the amino hip analogue of didemnin A

Disclosed is a synthetic method for the preparation of analogs of Didemnin A (1), particularly the Amino-Hip analog of Didemnin A, also known as “AipDidemnin A” (8). These compounds have the following structures:

ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF ANTI α-HYDRAZINO- AND α-AMINO-β-HYDROXYACIDS THROUGH "ELECTROPHILIC AMINATION" OF β-HYDROXYESTERS

β-Hydroxyesters 1a-d were transformed into corresponding dianions and condensed with di-t-butylazodicarboxylate to give anti protected α-hydrazino-β-hydroxyesters 2a-d with good diastereoselectivities (up to 94:6).Cleavage of protecting groups followed by ester hydrolysis gave the previously unknown anti α-hydrazino-β-hydroxyacids 4a-d, which were in turn converted by hydrogenolysis into anti α-amino-β-hydroxyacids 5a-d.Starting from (S) 1a, enantiomerically pure (2S,3S) allo-threonine 5a was obtained in good overall yields.On the contrary, reaction of silyl ketene acetal 10, derived from 1a, with a diazonium salt furnished predominantly the syn isomer, but in unsatisfactory yield.