61539-61-5

Usage

Uses

Used in Synthetic Chemistry:
1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene is used as a reagent for the synthesis of various complex organic molecules. Its unique structure allows it to participate in a range of reactions, such as cross-coupling, addition, and substitution reactions, making it a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Synthesis of Lasiodiplodin:
1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene is used as a key intermediate in the synthesis of Lasiodiplodin, a potent antileukemic macrolide. Lasiodiplodin exhibits significant anti-cancer properties and is being investigated for its potential use in the treatment of leukemia and other related blood disorders. 1,1-DiMethoxy-3-(triMethylsiloxy)-1,3-butadiene's reactivity and functional groups make it an ideal candidate for the construction of the complex Lasiodiplodin molecule.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 50473-61-5 4,4-dimethoxy-3-buten-2-one 

Downstream Products

• 65212-21-7 methyl (5-hydroxy-3-methoxy-2-methoxycarbonylphenyl)acetate 
• 28478-46-8 methyl 4-hydroxy-2-methoxybenzoate 
• 92511-96-1 1,7-bis(benzyloxy)-5-methoxy-4-naphthol 
• 88083-77-6 6-methoxy-2-phenyl-2,3-dihydropyran-4-onen 
• 28504-24-7 xanthopurpurin-1-methylether 
• 126-07-8 griseofulvin 
• 111737-33-8 4-(Cyanophenylmethylen)-6-methoxy-3,5-diphenylcyclohepta-2,6-dien-1-on 
• 111737-32-7 4-(Cyanophenylmethylen)-6-methoxy-3,5-diphenylcyclohepta-2,6-dien-1-on 
• 65212-19-3 4-hydroxy-6-methoxy-phthalic acid dimethyl ester 
• 65212-23-9 Methyl-2-methoxy-cyclohex-2-en-4-on-1-carboxylat 
• 65212-24-0 3-Methoxy-4-acetylcyclohex-2-en-1-on 
• 65565-48-2 2-chloro-5,7-dimethoxy-1,4-naphthoquinone 
• 71838-34-1 4-Hydroxy-2-methoxy-6-oct-7-enyl-benzoic acid methyl ester 

Relevant academic research and scientific papers

Addition of silyloxydienes to 2,6-dibromo-1,4-benzoquinone: An approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone

The synthesis of tetraoxygenated bromonaphthoquinones 6a, 6b, 6c, 6d, key intermediates for a synthesis of the 3C protease inhibitor, thysanone, were investigated. Addition of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene 8 to 2,6-dibromo-1,4-benzoquinone 10 in benzene afforded a mixture of naphthoquinone 6a, arising from Diels-Alder addition followed by aromatisation, and Michael adduct 12. The Michael adduct 12 predominated when THF was used as solvent whereas 6a predominated when benzene was used. Naphthoquinone 6a underwent benzylation to naphthoquinone 6c. Addition of 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene 9 to 2,6-dibromo-1,4-benzoquinone 10 followed by benzylation failed to afford the desired bromonaphthoquinone 6d yet methylation did afford naphthoquinone 6b. Bromonaphthoquinone 6d was finally prepared from naphthol 18, obtained from addition of diene 9 to 1,4-benzoquinone 17, followed by ortho-bromination and oxidation. Attempted Sakurai allylation of bromonaphthoquinone 6d afforded naphthodihydrofuran 21. A similar observation was observed for 2-carbomethoxy-1,4-naphthoquinone 22 that also underwent Sakurai allylation to afford naphthodihydrofuran 23. The structure of Michael adduct 12 was confirmed by X-ray crystallography.

2,3-Alkadiensaeureester als Dienophile; Anwendung bei der Synthese von (+)-(R)-Lasiodiplodin

Methyl 2,3-alkadienoates 2 are shown to react at 80 deg C with 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene (1) to give the adducts 3 in good yields.Rearrangement of 3, catalyzed by p-toluenesulfonic acid or by sodium methoxide, affords the 6-substitut