121964-06-5

Upstream product

• 1078118-69-0 C₁₈H₂₇NO₄ 
• 100572-69-8 (2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 

Downstream Products

• 120040-77-9 (2R,3S)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde 
• 121964-13-4 (2R,3S,4S)-5-Azido-1-O-benzoyl-3-O-benzyl-2-O-(methylsulfonyl)-4-methylpentane-1,2,3-triol 
• 122046-00-8 (2R,3S,4S)-5-Azido-3-O-benzyl-1,2-epoxy-4-methylpentan-3-ol 
• 121964-17-8 (2S,3S,4S)-5-Azido-3-O-benzyl-1,2-epoxy-4-methylpentan-3-ol 
• 121964-21-4 (1R,3S,4S,5R)-4-O-Benzyl-3-methyl-1-azabicyclo<3.1.0>hexan-4-ol 
• 122046-06-4 (1S,3S,4S,5S)-4-O-Benzyl-3-methyl-1-azabicyclo<3.1.0>hexan-4-ol 
• 121987-72-2 (2R,3S,4S)-5-Azido-3-O-benzyl-1,2-di-O-tosylpentane-1,2,3-triol 
• 121964-24-7 Toluene-4-sulfonic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester 
• 121964-16-7 Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester 
• 121964-08-7 (2R,3S,4S)-5-Azido-3-O-benzyl-4-methylpentane-1,2,3-triol 
• 121964-11-2 Methanesulfonic acid (2S,3S)-3-benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propyl ester 

Relevant academic research and scientific papers

Epoxyamide-based strategy for the synthesis of polypropionate-type frameworks

(Chemical Equation Presented) A new approach to the stereoselective synthesis of polypropionate-type frameworks is reported utilizing reactions of amide-stabilized sulfur ylides with chiral aldehydes. To establish a new strategy for macrolide fragment synthesis, the stereoselectivity of these reactions in the construction of epoxy amides was the most important aspect of this study. In this aspect, we found a strong influence of the protecting groups employed in the starting aldehydes upon the stereochemical outcome of their reactions with the sulfur ylide 1. Thus, numerous aldehydes showed remarkable stereofacial differentiation, providing a major diastereoisomer, in contrast to others that displayed a poor or no stereoselectivity. Despite the difficulties encountered for some cases with respect to their diastereomeric yields, we were able to prepare various stereotetrads and stereopentads, thus enhancing the synthetic value of this new methodology for the preparation of typical polypropionate frameworks found in many natural products, in particular the macrolide class of antibiotics.

Synthesis of Hydroxylated 1-Azabicyclohexane and Prolinol Derivatives by Stereo- and Regiocontrolled Staudinger Aminocyclization. Application to the Nonproteinogenic Amino Acid (2S,3S,4S)-3-Hydroxy-4-methylproline (HMP) and Its Enantiomer

On treatment with triphenylphosphine the azido epoxides 8/11 form enantio- and diastereomerically pure 1-azabicyclohexanes (9/12) via a Staudinger type aminocyclization reaction.Benzoic acid anhydride opens the aziridine ring in 9/12 to give prolin