methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

Base Information

Chemical Name:methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate
CAS No.:141765-23-3
Molecular Formula:C₂₅H₃₈O₆Si
Molecular Weight:462.659
Hs Code.:

Synonyms:methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

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Chemical Property of methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

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Technology Process of methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

There total 11 articles about methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 141765-22-2
methyl 7-benzyloxy-3a-hydroxy-3-(2-hydroxyethylidene)-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

: 141765-23-3
methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

: 100-39-0
benzyl bromide

: 141765-23-3
methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 75 percent / KH / tetrahydrofuran / 1 h / 0 °C

2: 1) p-TsOH*H₂O, 2) Et₃SiH, BF₃*OEt₂ / 1) 1.5h, reflux, 2) CH₂Cl₂, 8h, RT

3: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 25 min, 2) -78 deg C to RT

4: 98 percent / 2,6-lutidine, NEt₃ / CH₂Cl₂ / 0.75 h / 40 °C

5: 1) m-chloroperbenzoic acid, NaHCO₃, 2) Bu₄NF / 1) CH₂Cl₂, -20 deg C, 30 min, 2) THF, 0 deg C, 30 min

6: 72 percent / tetrahydrofuran / 4 h / -78 °C

7: 90 percent / pyridine, 4-pyrrolidinopyridine / CH₂Cl₂ / 24 h / 50 °C

8: 71 percent / benzoquinone / (CH₃CN)2PdCl₂ / acetonitrile / 36 h / Heating

9: 97 percent / K₂CO₃ / methanol / 0.33 h / Ambient temperature

10: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; triethylsilane; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; sodium hydrogencarbonate; potassium carbonate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

Reference yield:

: 141765-14-2
methyl 7-benzyloxy-3-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

: 141765-23-3
methyl 7-benzyloxy-3-(2-tert-butyldimethylsilyloxyethylidene)-3a-hydroxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 25 min, 2) -78 deg C to RT

2: 98 percent / 2,6-lutidine, NEt₃ / CH₂Cl₂ / 0.75 h / 40 °C

3: 1) m-chloroperbenzoic acid, NaHCO₃, 2) Bu₄NF / 1) CH₂Cl₂, -20 deg C, 30 min, 2) THF, 0 deg C, 30 min

4: 72 percent / tetrahydrofuran / 4 h / -78 °C

5: 90 percent / pyridine, 4-pyrrolidinopyridine / CH₂Cl₂ / 24 h / 50 °C

6: 71 percent / benzoquinone / (CH₃CN)2PdCl₂ / acetonitrile / 36 h / Heating

7: 97 percent / K₂CO₃ / methanol / 0.33 h / Ambient temperature

8: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; acetonitrile;