189164-67-8

Upstream product

• 189164-64-5 (R)-2-Methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-yn-3-ol 
• 189164-65-6 2-[(R)-4-(4-Methoxy-benzyloxy)-5-methyl-hex-2-ynyloxy]-tetrahydro-pyran 
• 189164-68-9 (R)-2-(4-Methoxy-benzyloxy)-3-methyl-butyric acid ethyl ester 
• 958018-56-9 (R)-2-(4-Methoxy-benzyloxy)-3-methyl-butyraldehyde 
• 189164-63-4 6-[(tetrahydro-2H-pyran-2-yl)oxy]-2-methylhex-4-yn-3-one 
• 184104-18-5 (2R)-2-(4-methoxybenzyl)oxy-3-methyl-1-butanol 
• 41056-46-6 1-isopropyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 129025-85-0 ethyl (R)-2-hydroxy-3-methylbutyrate 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 844494-24-2 (3S)-3-(4-methoxybenzyloxy)-2-methyl-hex-5-ene 
• 67760-85-4 (S)-2-methyl-5-hexen-3-ol 
• 844494-27-5 (4R,2E)-4-(p-methoxybenzyloxy)-5-methylhex-2-enyl acetate 
• 189164-69-0 (E)-(R)-4-(4-Methoxy-benzyloxy)-5-methyl-hex-2-enoic acid methyl ester 

Downstream Products

• 189164-76-9 (R)-4-((S)-1-{2-[(2R,3S,4R)-2-Hydroxy-3-methoxy-4-(4-methoxy-benzyloxy)-5-methyl-hexyl]-[1,3]dithian-2-yl}-ethyl)-[1,3]dioxolan-2-one 
• 189164-72-5 (2R,3S,4R)-2-hydroxy-3-methoxy-4-(4-methoxybenzyl)oxy-5-methyl-1-phenylhexane 
• 189164-74-7 (2R,3R,4R)-2-hydroxy-3-methoxy-4-(4-methoxybenzyl)oxy-5-methyl-1-hexanol 
• 189164-71-4 (2R,3R,4R)-1,2-epoxy-3-hydroxy-4-(4-methoxybenzyl)oxy-5-methylhexane 
• 170708-55-1 (2R,3S,6R,7S,8R)-6-(t-butyldimethylsiloxy)-1,2-dihydroxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane 
• 170708-51-7 (2R,3S,6R,7S,8R)-6-(t-butyldimethylsiloxy)-1,2-epoxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane 
• 170708-54-0 (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane 
• 170708-52-8 (2R,3R,4R)-1,2-epoxy-3-methoxy-4-(4-methoxybenzyl)oxy-5-methylhexane 
• 189164-70-3 (2R,3R,4R)-2,3-dihydroxy-4-(4-methoxybenzyl)oxy-5-methyl-1-hexanol 

Relevant academic research and scientific papers

Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules

(Chemical Equation Presented) A hydrocarbon oxidation approach has been applied to the construction of several linear (E)-allylic alcohols that have served as intermediates in the synthesis of natural products and natural product-like molecules. In the original syntheses, these intermediates were constructed using a standard Wittig-type olefination approach. We report here that routes to these same intermediates designed around a hydrocarbon oxidation approach are more efficient both in the total number of functional group manipulations (FGMs) and overall steps, as well as in the overall yield.

Synthetic studies on tautomycin synthesis of segment B

The synthesis of Segment B corresponding to the C26-C17 portion of tautomycin was accomplished by coupling reaction between the epoxide (Sub-segment B-l) and the dithiane (Subsegment B-2). The degradation product of tautomycin corresponding to the C26-C19 portion was also synthesized from Sub-segment B-1.