(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

Base Information

Chemical Name:(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester
CAS No.:872185-91-6
Molecular Formula:C₂₆H₃₆O₆Si
Molecular Weight:472.654
Hs Code.:

Synonyms:(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

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Chemical Property of (1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

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Technology Process of (1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

There total 6 articles about (1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester 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%

: (E)-1-pentenyl borate

: 872185-90-5
(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-iodo-5-oxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

: 872185-91-6
(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

Guidance literature:: With bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane; silver(l) oxide; In tetrahydrofuran; water; at 20 ℃; for 14h;
DOI:10.1021/jo0516436

Reference yield:

: 872185-87-0
(1S,2R,6S)-2-Hydroxy-4-iodo-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carbaldehyde

: 872185-91-6
(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[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 / 0 °C

2: 97 percent / NaClO₂; NaHPO₄; 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 / Pd(PhCN)2Cl₂; Ph₃As; Ag₂O / tetrahydrofuran; H₂O / 14 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; bis(benzonitrile)palladium(II) dichloride; 2-methyl-but-2-ene; triphenyl-arsane; camphor-10-sulfonic acid; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 4: Suzuki coupling;
DOI:10.1021/jo0516436

Reference yield:

: 872185-86-9
(1S,5R,6S)-5-hydroxy-4-(hydroxymethyl)-3-iodo-7-oxabicyclo[4.1.0]hept-3-en-2-one

: 872185-91-6
(1R,2R,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-oxo-4-(pent-1-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 5 steps

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

2: 170 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3: 97 percent / NaClO₂; NaHPO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

4: 85 percent / CH₂Cl₂ / 1 h / 0 °C

5: 97 percent / Pd(PhCN)2Cl₂; Ph₃As; Ag₂O / tetrahydrofuran; H₂O / 14 h / 20 °C

With 2,6-dimethylpyridine; manganese(IV) oxide; sodium chlorite; bis(benzonitrile)palladium(II) dichloride; 2-methyl-but-2-ene; triphenyl-arsane; camphor-10-sulfonic acid; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 5: Suzuki coupling;
DOI:10.1021/jo0516436