97363-18-3

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 97363-17-2 1-Benzyl-4-(2-benzyloxy-ethyl)-3-((R)-1-hydroxy-ethyl)-azetidin-2-one 
• 108053-21-0 (3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-ethynyl-azetidin-2-one 
• 97363-16-1 3-Benzylamino-5-benzyloxy-2-((R)-1-hydroxy-ethyl)-pentanoic acid 
• 97363-15-0 Benzyl-[3-benzyloxy-prop-(E)-ylidene]-amine 
• 107544-36-5 3-Benzylamino-2-((R)-1-hydroxy-ethyl)-5-trimethylsilanyl-pent-4-ynethioic acid S-phenyl ester 
• 105780-06-1 (3S,4S)-1-Benzyl-4-ethynyl-3-((R)-1-hydroxy-ethyl)-azetidin-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 97363-15-0 C₁₇H₁₉NO 
• 97381-27-6 3-Benzylamino-5-benzyloxy-2-((R)-1-hydroxy-ethyl)-pentanethioic acid S-phenyl ester 
• 101911-11-9 N-<3-(trimethylsilyl)-2-propynylidene>benzylamine 
• 100-39-0 benzyl bromide 
• 256371-18-3 (3S,4R)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-vinyl-azetidin-2-one 

Downstream Products

• 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).