7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-4-(1E)-1-pentenyl-, (4-methoxyphenyl)methyl ester, (1S,2S,6R)-

Base Information

Chemical Name:7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-4-(1E)-1-pentenyl-, (4-methoxyphenyl)methyl ester, (1S,2S,6R)-
CAS No.:805325-71-7
Molecular Formula:C26H36O6Si
Molecular Weight:472.654
Hs Code.:

7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid,
2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-4-(1E)-1-pentenyl-,
(4-methoxyphenyl)methyl ester, (1S,2S,6R)-

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Chemical Property of 7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-4-(1E)-1-pentenyl-, (4-methoxyphenyl)methyl ester, (1S,2S,6R)-

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Technology Process of 7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-4-(1E)-1-pentenyl-, (4-methoxyphenyl)methyl ester, (1S,2S,6R)-

There total 7 articles about 7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-4-(1E)-1-pentenyl-, (4-methoxyphenyl)methyl ester, (1S,2S,6R)- 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: 97.0%

: 104376-24-1,59239-44-0
(E)-1-pentenylboronic acid

: 805325-70-6
(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-4-iodo-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

: 805325-71-7
(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

Guidance literature:: With triphenyl-arsane; silver(l) oxide; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; water; at 20 ℃; for 14h;
DOI:10.1021/ol0481479

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 805325-71-7
(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 170 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -30 °C

2: 97 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

3: 85 percent / CH₂Cl₂ / 1 h / 0 °C

4: 97 percent / Ag₂O; Ph₃As / Pd(PhCN)2Cl₂ / tetrahydrofuran; H₂O / 14 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; triphenyl-arsane; silver(l) oxide; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 4: Suzuki coupling;
DOI:10.1021/ol0481479

Reference yield:

: 488808-31-7
(4R,6R,7S)-2-iodo-9,9-dimethyl-5,8,10-trioxatricyclo[5.4.0.0^4,6]undec-1-en-3-one

: 805325-71-7
(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

2: MnO₂ / acetonitrile / 0.17 h / 0 °C

3: 170 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -30 °C

4: 97 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

5: 85 percent / CH₂Cl₂ / 1 h / 0 °C

6: 97 percent / Ag₂O; Ph₃As / Pd(PhCN)2Cl₂ / tetrahydrofuran; H₂O / 14 h / 20 °C

With 2,6-dimethylpyridine; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; triphenyl-arsane; trifluoroacetic acid; silver(l) oxide; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 6: Suzuki coupling;
DOI:10.1021/ol0481479