97381-27-6

Upstream product

• 97363-14-9 (R)-3-hydroxybutyrate thiophenyl ester 
• 97363-15-0 Benzyl-[3-benzyloxy-prop-(E)-ylidene]-amine 
• 97363-15-0 C₁₇H₁₉NO 
• 108070-88-8 3-(tert-butyldimethylsilyl) butyrate thiophenyl ester 
• 108-98-5 thiophenol 

Downstream Products

• 97363-17-2 1-Benzyl-4-(2-benzyloxy-ethyl)-3-((R)-1-hydroxy-ethyl)-azetidin-2-one 
• 97363-16-1 3-Benzylamino-5-benzyloxy-2-((R)-1-hydroxy-ethyl)-pentanoic acid 
• 97414-48-7 (3S,4S)-1-Benzyl-4-(2-benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one 
• 97363-18-3 (3S,4R)-1-Benzyl-4-(2-benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one 
• 97414-47-6 (3R,4R)-1-Benzyl-4-(2-benzyloxy-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one 
• 78477-86-8 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone 

Relevant academic research and scientific papers

ON THE STEREOCHEMICAL COURSE OF VINYLOXYBORANE-IMINE CONDENSATION - THE STEREOSELECTIVE FORMATION OF THREO β-AMINO ACID DERIVATIVES

While reaction of Z(O)-vinyloxyboranes with aldehydes gives erythro aldols highly selectively, it has been found that condensation of Z(O)-vinyloxyboranes with imines provides threo β-amino acid derivatives in a highly selective manner.

Stereocontrolled synthesis of (+)-thienamycin from 3(R)-hydroxybutyric acid

The vinyloxyborane(5), prepared from (+)-S-phenyl-3(R)-butanethioate, 9-BBN triflate and diisopropylethylamine, reacted with N-(3-benzyloxypropylidene)benzylamine to give the β-benzylamino thiol ester(6) in a moderate yield, which was efficiently converted to the optically pure thienamycin intermediate(10).