90369-06-5

Upstream product

• 51326-51-3 4-(tetrahydropyran-2-yloxy)butan-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 41049-30-3 2-(4-iodobutoxy)tetrahydropyran 
• 603-35-0 triphenylphosphine 

Downstream Products

• 623926-63-6 tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane 
• 623926-36-3 (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-(tert-butyldimethylsilanyloxy)-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraen-1-yl tetrahydropyran-2-yl ether 
• 623926-52-3 [(6Z,11Z)-(1S,2S,3S,8S,9S,10S)-3,9-Bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-15-(tetrahydro-pyran-2-yloxy)-pentadeca-6,11-dienyloxy]-tert-butyl-dimethyl-silane 
• 623926-65-8 Carbamic acid (4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1S,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyl ester 
• 623926-40-9 carbamic acid (Z,Z)-(1S,2S,3R,8S,9S,10S)-3,9-bis(4-methoxybenzyloxy)-2,8,10-trimethyl-1-[(Z)-(S)-1-methylpenta-2,4-dienyl]-15-(tetrahydropyran-2-yloxy)pentadeca-6,11-dienyl ester 
• 623926-66-9 Acetic acid (4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1S,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyl ester 
• 623926-41-0 Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-15-(tetrahydro-pyran-2-yloxy)-pentadeca-6,11-dienyl ester 
• 623926-64-7 (3Z,11Z,16Z)-(5S,6S,7S,8R,13S,14S,15S)-6,14-Bis-(4-methoxy-benzyloxy)-5,7,13,15-tetramethyl-20-(tetrahydro-pyran-2-yloxy)-icosa-1,3,11,16-tetraen-8-ol 
• 623926-39-6 (Z,Z,Z)-(5S,6S,7S,8R,13S,14S,15S)-8,14-bis(4-methoxybenzyloxy)-5,7,13,15-tetramethyl-20-(tetrahydropyran-2-yloxy)eicosa-1,3,11,16-tetraen-6-ol 
• 623926-53-4 (Z,Z,Z)-(5S,6S,7S,8S,13S,14S,15S)-8,14-bis(4-methoxybenzyloxy)-5,7,13,15-tetramethyl-20-(tetrahydropyran-2-yloxy)eicosa-1,3,11,16-tetraen-6-ol 
• 623926-37-4 2-[(Z)-(6S,7S,8R)-9-Iodo-7-(4-methoxy-benzyloxy)-6,8-dimethyl-non-4-enyloxy]-tetrahydro-pyran 
• 623926-34-1 (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol 
• 444682-17-1 (Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal 
• 444682-16-0 (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether 

Relevant academic research and scientific papers

Syntheses, characterizations, and biological activities of tetradeca-4,8-dien-1-yl acetates as sex attractants of leaf-mining moth of the genus Phyllonorycter (Lepidoptera: Gracillariidae)

The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca-4,8-dien-1-ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB-1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB-WAX column. The isomers of tetradeca-4,8-dien-1-yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB-1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB-WAX columns. Field-screening tests for attractiveness of tetradeca-4,8-dien-1-yl acetates revealed that (4Z,8E)-tetradeca-4,8-dien-1-yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)-Tetradeca-4,8-dien-1-yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)-tetradeca-4,8-dien-1-yl acetate was attractive to Ph. cerasicolella males.

Synthesis and biological assessment of simplified analogues of the potent microtubule stabilizer (+)-discodermolide

An efficient, convergent and stereocontrolled synthesis of simplified analogues of the potent antimitotic agent (+)-discodermolide has been achieved and several small libraries have been prepared. In all the libraries, the discodermolide methyl groups at

Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis

(matrix presented) Four analogues made in one synthesis Four truncated analogues of the natural product discodermolide were synthesized in a single synthetic sequence. Precursors bearing four different groups at C22, each with a unique fluorous p-methoxyb