631919-29-4

Upstream product

• 145958-02-7 (2S,4S)-2-phenyl-1,3-dioxane-4-carboxaldehyde 
• 79414-15-6 2-(triphenyl-λ5-phosphine ylide) 2-(trimethylsilyl)ethyl acetate 

Downstream Products

• 631919-33-0 (1'S,1R,2R)-2-[3-(1-phenyl-1H-tetrazole-5-sulfonyl)-1'-triethylsilanyloxy-propyl]-cyclopentane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-59-0 (1'S,1R,2R)-2-[3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-1'-triethylsilanyloxy-propyl]-cyclopentane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-58-9 (1'S,1R,2R)-2-[1'-hydroxy-3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-propyl]-cyclopentane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 631919-31-8 2(R)-allyl-3(R)-(2(S)-phenyl-[1,3]dioxan-4(S)-yl)-pent-4-enoic acid 2-trimethylsilanyl-ethyl ester 
• 631919-32-9 1(R),2(R)-(2(S)-phenyl-[1,3]dioxan-4(S)-yl)-cyclopent-3-enecarboxylic acid 2-trimethylsilanyl-ethyl ester 

Relevant academic research and scientific papers

Application of Conformation Design in Acyclic Stereoselection: Total Synthesis of Borrelidin as the Crystalline Benzene Solvate

The total synthesis of (-)-borrelidin (treponemycin), a structurally distinct 18-membered macrolide antibiotic, has been achieved. It was isolated as the crystalline benzene solvate, and its structure was confirmed by a single-crystal X-ray analysis. The deoxypropionate subunit consisting of four alternating C-methyl groups with a C4-C10 syn/syn/anti orientation was elaborated by a new method of iterative cuprate additions to acyclic α,β-unsaturated esters relying on two consequtive 1,3-inductions and starting with D-glyceraldehyde as the chiral progenitor. The unique Z/E cyanodiene unit was obtained as a single isomer by application of the Still-Gennari olefination protocol. The γ-hydroxycyclopentane carboxylic acid subunit was prepared from L-malic acid utilizing a sequential introduction of C-vinyl and C-allyl groups, capitalizing on 1,2-induction in an acyclic α,β-unsaturated ester and carbocyclization by a Grubbs ring closure metathesis reaction. The prevalence of 1,3-syn-disposed deoxypropionate triads in the cuprate additions is rationalized on the basis of minimized syn-pentane interactions in the transition states. A virtual diamond lattice was used as a visual tool to portray the low-energy conformations of the acyclic substrates, and corroborated by 1H NMR homodecoupling studies.