215370-56-2

Upstream product

• 1312696-36-8 (3S,4R)-3-methoxy-7-((4-methoxybenzyloxy)methyl)-4-triethylsilyloxyocta-1,7-diene 
• 1312696-38-0 (3S,4R)-1-hydroxymethyl-3-methoxy-4-(triethylsilyloxy)cyclohex-1-ene 
• 215370-51-7 (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 215370-54-0 (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester 
• 215370-52-8 (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enecarboxylic acid methyl ester 
• 215370-45-9 Benzoic acid (1S,4R,5R)-1-hydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester 
• 215370-49-3 (R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester 
• 215370-46-0 (1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol 
• 215370-53-9 (3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene 
• 105539-78-4 (1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate 
• 91738-34-0 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 994-30-9 triethylsilyl chloride 
• 870862-57-0 (1R,2R,3S,4S)-1-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexane 
• 870862-47-8 (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose 

Downstream Products

• 19683-98-8 (-)-ovalicin 
• 1053729-00-2 Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester 

Relevant academic research and scientific papers

Simple and efficient synthesis of highly functionalized cyclohexanes; Formal total synthesis of ovalicin and fumagillin

Two chiral cyclohexanes 4 and 6, which are key intermediates for the total synthesis of ovalicin 1 and fumagillin 2, respectively, were synthesized from (2R,3S) 1,2-epoxy-4-penten-3-ol. The key steps involve an efficient construction of divinylalcohol 7 u

Synthesis of ovalicin starting from D-mannose

A new synthesis of epoxyketone 22 is described that is a key intermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11 and 12 obtained f

Enantioselective formal synthesis of (-)-ovalicin using quinic acid as a chiral template

The key intermediate 18 for the synthesis of (-)-ovalicin was synthesized using (-)-quinic acid as the chiral source, through a series of stereocontrolled and efficient chemical reactions, thus establishing a new, formal synthesis of the natural target. The featuring spirocyclic epoxide function has been installed by internal Williamson ether synthesis using the functionalities originally present at C-1 of (-)-quinic acid after the appropriate adjustments required to introduce the necessary functionality at C-2.