Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

Base Information

Chemical Name:Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one
CAS No.:247910-74-3
Molecular Formula:C₂₄H₂₅BrO₃Si
Molecular Weight:469.45
Hs Code.:

Synonyms:Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

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Chemical Property of Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

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Technology Process of Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

There total 9 articles about Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one 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:

: 115869-43-7
(tert-butyldiphenylsilanyloxy)acetaldehyde

: [Z-2-(4-Bromo-5-oxofuran-2(5H)-ylidene)ethyl]triphenylphosphonium bromide

: 247910-74-3
Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

: 247910-73-2
Z-3-Bromo-5-[trans-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

Guidance literature:: [Z-2-(4-Bromo-5-oxofuran-2(5H)-ylidene)ethyl]triphenylphosphonium bromide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

(tert-butyldiphenylsilanyloxy)acetaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Title compound not separated from byproducts;

Reference yield:

: 115869-43-7
(tert-butyldiphenylsilanyloxy)acetaldehyde

: [E/Z-2-(4-Bromo-5-oxofuran-2(5H)-ylidene)ethyl]triphenylphosphonium bromide

: 247910-74-3
Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

: 247910-73-2
Z-3-Bromo-5-[trans-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

Guidance literature:: [E/Z-2-(4-Bromo-5-oxofuran-2(5H)-ylidene)ethyl]triphenylphosphonium bromide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

(tert-butyldiphenylsilanyloxy)acetaldehyde; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; Title compound not separated from byproducts;

Reference yield:

: 69617-71-6
3,5-di-O-acetyl-2,6-dibromo-2,6-dideoxy-D-glucono-1,4-lactone

: 247910-74-3
Z-3-Bromo-5-[cis-4-(tert-butyldiphenylsilyloxy)but-2-enylidene]furan-2(5H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: MeOH / 12 h

2.1: pyridine; Tf₂O / CH₂Cl₂

3.1: 96 percent / acetonitrile / 0.17 h

4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 1 h / -78 - 20 °C

With pyridine; methanol; trifluoromethylsulfonic anhydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile; 1.1: Deacetylation / 2.1: Dehydration / 3.1: Substitution / 4.1: Metallation / 4.2: Substitution;