(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

Base Information

Chemical Name:(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate
CAS No.:864270-17-7
Molecular Formula:C₃₅H₅₀O₇Si
Molecular Weight:610.863
Hs Code.:

(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

Synonyms:(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

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Chemical Property of (3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

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Technology Process of (3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

There total 17 articles about (3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate 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: 80.0%

: 864270-14-4
5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-3-{(3S)-1-hydroxy-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl}furan-2(5H)-one

: 108-24-7
acetic anhydride

: 864270-17-7
(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1039/b504545b

Reference yield:

: 864182-74-1
(3RS)-3-(isopropenyl)pentanolide

: 864270-17-7
(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

Guidance literature:: Multi-step reaction with 9 steps

1.1: Me₃Al / hexane; CH₂Cl₂ / 0.25 h / 0 °C

1.2: 39 percent / hexane; CH₂Cl₂ / 16 h / 20 °C

2.1: 85 percent / pyridinium p-toluenesulfonate / toluene / 16 h / Heating

3.1: 88 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.1: t-BuLi / pentane; diethyl ether / -78 - 0 °C

4.2: 64 percent / pentane; diethyl ether / 0 - 20 °C

5.1: 64 percent / pyridinium p-toluenesulfonate / benzene / 2 h / Heating

6.1: 95 percent / dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 60 percent / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: 96 percent / aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

9.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 °C

With dmap; oxalyl dichloride; dihydrogen peroxide; trimethylaluminum; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; benzene; 6.1: Swern oxidation;
DOI:10.1039/b504545b

Reference yield:

: 864182-76-3
(3S)-3-(isopropenyl)pentan-5-olide

: 864270-17-7
(3R)-1-{5-[(2E)-4-(tert-butyldimethylsilyloxy)-2-methylbut-2-enyl]-2-oxo-2,5-dihydrofuran-3-yl}-4-methyl-3-[(5-methylene-2-phenyl-1,3-dioxan-4-yl)methyl]pent-4-enyl acetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.1: t-BuLi / pentane; diethyl ether / -78 - 0 °C

2.2: 64 percent / pentane; diethyl ether / 0 - 20 °C

3.1: 64 percent / pyridinium p-toluenesulfonate / benzene / 2 h / Heating

4.1: 95 percent / dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

5.2: 60 percent / tetrahydrofuran; hexane / 1 h / -78 °C

6.1: 96 percent / aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

7.1: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 °C

With dmap; oxalyl dichloride; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; benzene; 4.1: Swern oxidation;
DOI:10.1039/b504545b