ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

Base Information

Chemical Name:ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate
CAS No.:445235-69-8
Molecular Formula:C₃₂H₅₂O₈Si
Molecular Weight:592.846
Hs Code.:

Synonyms:ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

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Chemical Property of ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

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Technology Process of ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

There total 10 articles about ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate 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:

: 445235-61-0
(2E,5R)-5,6-isopropylidenedioxy-2-methyl-2-hexen-1-ol

: 445235-69-8
ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 2.66 g / triethylamine / CH₂Cl₂ / 2 h / ice-cooling

2.1: aq. (DHQ)2PHAL; methanesulfonamide; K₂CO₃ / K₂OsO₂(OH)4; K₃Fe(CN)6 / 2-methyl-propan-2-ol / 2 h / 0 °C

3.1: p-TsOH*H₂O / 1 h / 20 °C

4.1: 408 mg / Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

5.1: dibutyltin oxide / toluene / 12 h / Heating

5.2: 84 percent / tetrabutylammonium iodide / toluene / 1.5 h / Heating

6.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

7.1: 676 mg / aq. KOH / methanol; tetrahydrofuran / 1 h / 20 °C

8.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4A / CH₂Cl₂ / 1.5 h / 20 °C

9.1: 402 mg / DBU; lithium chloride / acetonitrile / 2.5 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; zinc(II) nitrate; tetrapropylammonium perruthennate; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; 4 A molecular sieve; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 9.1: Horner-Emmons reaction;
DOI:10.1021/ja030133v

Reference yield:

: 445235-60-9
methyl (2E,5R)-5,6-isopropylidenedioxy-2-methyl-2-hexenoate

: 445235-69-8
ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: LiAlH₄ / diethyl ether / 2 h / ice-cooling

2.1: 2.66 g / triethylamine / CH₂Cl₂ / 2 h / ice-cooling

3.1: aq. (DHQ)2PHAL; methanesulfonamide; K₂CO₃ / K₂OsO₂(OH)4; K₃Fe(CN)6 / 2-methyl-propan-2-ol / 2 h / 0 °C

4.1: p-TsOH*H₂O / 1 h / 20 °C

5.1: 408 mg / Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

6.1: dibutyltin oxide / toluene / 12 h / Heating

6.2: 84 percent / tetrabutylammonium iodide / toluene / 1.5 h / Heating

7.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

8.1: 676 mg / aq. KOH / methanol; tetrahydrofuran / 1 h / 20 °C

9.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4A / CH₂Cl₂ / 1.5 h / 20 °C

10.1: 402 mg / DBU; lithium chloride / acetonitrile / 2.5 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; zinc(II) nitrate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; 4 A molecular sieve; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 10.1: Horner-Emmons reaction;
DOI:10.1021/ja030133v

Reference yield:

: 445235-62-1
(2E,5R)-1-benzoyloxy-5,6-isopropylidenedioxy-2-methyl-2-hexene

: 445235-69-8
ethyl (6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8,9-isopropylidenedioxy-12-p-methoxybenzyloxy-8-methyl-5-oxo-6-dodecenoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: aq. (DHQ)2PHAL; methanesulfonamide; K₂CO₃ / K₂OsO₂(OH)4; K₃Fe(CN)6 / 2-methyl-propan-2-ol / 2 h / 0 °C

2.1: p-TsOH*H₂O / 1 h / 20 °C

3.1: 408 mg / Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

4.1: dibutyltin oxide / toluene / 12 h / Heating

4.2: 84 percent / tetrabutylammonium iodide / toluene / 1.5 h / Heating

5.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

6.1: 676 mg / aq. KOH / methanol; tetrahydrofuran / 1 h / 20 °C

7.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4A / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 402 mg / DBU; lithium chloride / acetonitrile / 2.5 h / 20 °C

With 2,6-dimethylpyridine; potassium hydroxide; zinc(II) nitrate; tetrapropylammonium perruthennate; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; 4 A molecular sieve; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 8.1: Horner-Emmons reaction;
DOI:10.1021/ja030133v