7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-iodo-5-oxo-, (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]-4-iodo-5-oxo-, (4-methoxyphenyl)methyl ester, (1S,2S,6R)-
CAS No.:805325-70-6
Molecular Formula:C21H27IO6Si
Molecular Weight:530.432
Hs Code.:

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

There total 6 articles about 7-Oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-iodo-5-oxo-, (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: 85.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 805325-66-0
(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-4-iodo-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic 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

Guidance literature:: In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol0481479

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: Multi-step reaction with 3 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

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In dichloromethane; water; tert-butyl alcohol;
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

: 805325-70-6
(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

Guidance literature:: Multi-step reaction with 5 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

With 2,6-dimethylpyridine; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trifluoroacetic acid; In dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ol0481479