methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate

Base Information

Chemical Name:methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate
CAS No.:732301-92-7
Molecular Formula:C₂₉H₄₁BO₅Si
Molecular Weight:508.538
Hs Code.:

Synonyms:methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate

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Chemical Property of methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate

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Technology Process of methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate

There total 2 articles about methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

: 70557-99-2
2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 917-54-4
methyllithium

: 403805-83-4
methyl 4-(tert-butyldiphenylsilyloxy)-2-butynoate

: 732301-92-7
methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate

Guidance literature:: methyllithium; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.166667h;

methyl 4-(tert-butyldiphenylsilyloxy)-2-butynoate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 2h;
DOI:10.1021/jo049773m

Reference yield:

: 70557-99-2
2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 15681-48-8
lithium dimethylcuprate

: 403805-83-4
methyl 4-(tert-butyldiphenylsilyloxy)-2-butynoate

: trans-(Ph₂(CH₃)3CSiOCH₂)MeCCCOOMe(CH₂B(OCMe₂)2)

: 732301-92-7
methyl (2Z)-4-(tert-butyldiphenylsilyloxy)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoate

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78°C in the presence of 9 equiv. of HMPA; chromy., as mixt. of cis- and trans-isomers with >20:1 ratio (determinedby NMR);
DOI:10.1021/ja016391e