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}-3-(phenylseleno)dihydrofuran-2(3H)-one

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Chemical Name: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}-3-(phenylseleno)dihydrofuran-2(3H)-one
CAS No.:864270-13-3
Molecular Formula:C₃₉H₅₄O₆SeSi
Molecular Weight:725.9
Hs Code.:

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}-3-(phenylseleno)dihydrofuran-2(3H)-one

Synonyms: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}-3-(phenylseleno)dihydrofuran-2(3H)-one

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Chemical Property of 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}-3-(phenylseleno)dihydrofuran-2(3H)-one

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Technology Process of 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}-3-(phenylseleno)dihydrofuran-2(3H)-one

There total 15 articles about 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}-3-(phenylseleno)dihydrofuran-2(3H)-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: 60.0%

: 864182-71-8
(3S)-3-isopropenyl-5,7-O-benzylidene-6-(methylene)heptanal

: 864182-70-7
(4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide

: 864270-13-3
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}-3-(phenylseleno)dihydrofuran-2(3H)-one

Guidance literature:: (4R)-2-(phenylselenyl)-6-methyl-8-(tert-butyldimethylsilyloxy)oct-6-en-4-olide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(3S)-3-isopropenyl-5,7-O-benzylidene-6-(methylene)heptanal; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1039/b504545b

Reference yield:

: 864182-77-4
3-(isopropenyl)tetrahydropyran-2-ol

: 864270-13-3
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}-3-(phenylseleno)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 64 percent / pentane; diethyl ether / 0 - 20 °C

2.1: 64 percent / pyridinium p-toluenesulfonate / benzene / 2 h / Heating

3.1: 95 percent / dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

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

4.2: 60 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With oxalyl dichloride; tert.-butyl lithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; benzene; 3.1: Swern oxidation;
DOI:10.1039/b504545b

Reference yield:

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

: 864270-13-3
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}-3-(phenylseleno)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 7 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

With oxalyl dichloride; 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