76771-95-4

Upstream product

• 10160-24-4 7-bromoheptyl alcohol 
• 603-35-0 triphenylphosphine 

Downstream Products

• 37011-95-3 (7E)-tetradec-7-en-1-ol 
• 40642-43-1 (Z)-tetradec-7-en-1-ol 
• 16695-40-2 (E)-7-dodecene-1-ol 
• 20056-92-2 (Z)-7-dodecenol 
• 91920-90-0 1-acetoxy 7E,9Z-dodecadiene 
• 50933-33-0 (7E/Z,11Z/E)-7,11-hexadecadien-1-yl acetate 
• 269725-96-4 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-octyl ether 
• 24546-19-8 Δ7-hexadecenol 
• 24546-19-8 (E)-7-hexadecen-1-ol 

Relevant academic research and scientific papers

Synthesis of phytyl- and chroman-derivatized photoaffinity labels based on α-tocopherol

Photoaffinity analogues of α-tocopherol have been prepared by substituting photosensitive functional groups at either the terminus of an alkyl chain of varying length mimicking the phytyl tail or on C-3 of the chroman portion of tocopherol. The alkyl chain-modified compounds 2a-d contain a hexyl to nonyl alkyl chain extending from C-2 of the chroman, terminating in a tetrafluoroazidobenzyloxy group. These compounds were prepared starting from the commercially available Trolox acid 4, followed by esterification, protection, and reduction to the silyl-protected Trolox aldehyde 7, which was coupled using Wittig chemistry to different ω- hydroxyphosphonium bromides. Reduction of the alkene product, coupling with p-azidotetrafluorobenzyl bromide, and deprotection of the phenolic silyl group gave compounds 2a-d in excellent yields. Chroman-functionalized photoaffinity labels were synthesized starting from the protected tocopherol chromene 16b which was a key intermediate for preparation of a 3-hydroxy derivative, either by reduction of epoxides produced directly with Jacobsen's catalysts or by treatment with NBS in wet DME to give two stereoisomeric bromohydrins which were cyclized and reduced to give the phenol-protected C-3 alcohols 19a,b. These alcohols were then converted to diazoacetate esters, and the protecting group was removed to give 3-diazoacetoxy α-tocopherols 3a,b.

Investigation of Aliphatic Dienes by Chemical Ionization with Nitric Oxide

It is shown that the position of the double bond close to the hydrocarbon end of an aliphatic diene functionalized at C(1) can readily be determined by chemical ionization with NO+.Owing to the low abundance of the ions characteristic for the position of the other double bond, its localization may be difficult.Measurement of the chemical ionization (nitric oxide as reagent gas) spectra of the corresponding epoxides or collision activation studies can help.