74500-59-7

Upstream product

• 105198-40-1 ethyl (2E,4S)-4-<(tert-butyldimethylsilyl)oxy>-2-pentenoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 87727-28-4 (S)-2-tert-butyl-dimethyl-silanyloxy propanal 
• 74500-56-4 (S)-5-Trityloxy-pentan-2-ol 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 74500-57-5 (S)-4-t-butyldimethylsilyloxy-1-trityloxypentane 
• 52813-64-6 (R)-5-(chloromethyl)tetrahydro-2-furanone 
• 105198-38-7 ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate 
• 879571-57-0 (1,1-dimethylethyl)dimethyl{[(1S)-1-methylpent-4-enyl]oxy}silane 
• 327978-02-9 ethyl (4S)-4-(tert-butyl(dimethyl)silyloxy)pentanoate 
• 74500-58-6 (4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-pentanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 626-95-9 (2S)-2-methylbutane-1,4-diol 

Downstream Products

• 211988-85-1 (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methanol 
• 211988-86-2 (2S,4S,6R)-6-[((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl-4-methylbenzenesulfonate 
• 211988-80-6 methyl 3-[(2R,4S,6R)-6-((Z,6S)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-heptenyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-2-(phenylsulfonyl)propanoate 
• 211988-77-1 (1R,2Z,7S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-[(2S)-5-oxo-4-(phenylsulfonyl)tetrahydro-2-furanyl]methyl-2-octenyl 4-methoxybenzoate 
• 211988-76-0 (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one 
• 155853-18-2 {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane 
• 20350-15-6 (+)-brefeldin A 

Relevant academic research and scientific papers

Novel Type of Sex Pheromone Structure Identified from Stigmella malella (Stainton) (Lepidoptera: Nepticulidae)

Short-chain unsaturated chiral methyl carbinols are identified as a new class of lepidopteran pheromone components. The natural female-produced pheromone of the banded apple pigmy Stigmella malella (= Nepticula malella) (Stainton) (Lepidoptera: Nepticulid

Total synthesis of (+)-brefeldin A

The total synthesis of (+)-brefeldin A has been accomplished via 15 linear steps in a 7.9% overall yield from the known Weinreb amide 6. The key parts of this approach include the stereoselective construction of the cis-disubstituted hydroxycyclopentane skeleton and the direct introduction of the C1-C3 acrylate moiety using a new variant of a trans-vinylogous acyl anion equivalent.

A formal synthesis of (+)-brefeldin A

A formal synthesis of (+)-brefeldin A has been achieved via stereoselective construction of hydroxycyclopentane skeleton possessing the requisite hydroxyheptenyl side chain. The highly advanced intermediate 2 has been synthesized from the known Weinreb amide in 19% overall yield of 11 steps.

Stereocontrolled Synthesis of Dihydroxycyclopentane Derivative: Enantioselective Synthesis of (+)-Brefeldin A

A novel enantioselective synthesis of (+)-brefeldin A was achieved via stereocontrolled one-pot synthesis of a dihydroxycyclopentane derivative from allyl phenyl sulfone and chiral diepoxide.