(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

Base Information

Chemical Name:(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one
CAS No.:172996-24-6
Molecular Formula:C₃₂H₄₆O₄Si
Molecular Weight:522.8
Hs Code.:

(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

Synonyms:(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

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Chemical Property of (3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

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Technology Process of (3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

There total 14 articles about (3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one 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:

: 61305-35-9
(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

: 172996-24-6
(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

Guidance literature:: Multi-step reaction with 14 steps

1: 99 percent / CuBr-Me₂S complex, HMPA / tetrahydrofuran / 1 h / -78 °C

2: 1.) MeLi / 1.) THF, -20 deg C, 0.5 h, 2.) THF, -20 deg, overnight

3: 87 percent / triethylamine, triphenylphosphine, palladium acetate / dimethylformamide / 3 h / 760 Torr

4: 85 percent / p-toluenesulfonic acid / acetone / 36 h / Ambient temperature

5: 1). potasium tert-butoxide 2.)K₂CO₃ / 1.) benzene, RT, 10 min, 2.) MeOH, overnight

6: 93 percent / p-toluenesulfonic acid, pyridine / methanol / 8 h

7: 1.) N-methylomorpholine N-oxide, N-methylmorpholine, 4 Angstroem molecular sieves , 2.) tetrapropylamoniumperruthenate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, overnight

8: LDA / tetrahydrofuran

9: NBS, propylene oxide, Et₃N

10: 78 percent / 30percent H₂O₂, 1 N NaOH / CH₂Cl₂; methanol / 2 h / -10 - 10 °C

11: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h

12: amonium formate, Pd₂(dba)3*CHCl₃, tributylphosphine / dioxane / 1 h / Heating

13: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,

14: 1.) 1,7 M tert-butyllithium / 1.) THF, pentane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

With 4-methyl-morpholine; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; N-Bromosuccinimide; tetrapropylammonium perruthennate; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; methyllithium; dihydrogen peroxide; tert.-butyl lithium; ammonium formate; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja9533454

Reference yield:

: 3-(2-methyl-1,3-dioxolan-2-yl)prop-1-yl magnesium bromide

: 172996-24-6
(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

Guidance literature:: Multi-step reaction with 14 steps

1: 99 percent / CuBr-Me₂S complex, HMPA / tetrahydrofuran / 1 h / -78 °C

2: 1.) MeLi / 1.) THF, -20 deg C, 0.5 h, 2.) THF, -20 deg, overnight

3: 87 percent / triethylamine, triphenylphosphine, palladium acetate / dimethylformamide / 3 h / 760 Torr

4: 85 percent / p-toluenesulfonic acid / acetone / 36 h / Ambient temperature

5: 1). potasium tert-butoxide 2.)K₂CO₃ / 1.) benzene, RT, 10 min, 2.) MeOH, overnight

6: 93 percent / p-toluenesulfonic acid, pyridine / methanol / 8 h

7: 1.) N-methylomorpholine N-oxide, N-methylmorpholine, 4 Angstroem molecular sieves , 2.) tetrapropylamoniumperruthenate / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, overnight

8: LDA / tetrahydrofuran

9: NBS, propylene oxide, Et₃N

10: 78 percent / 30percent H₂O₂, 1 N NaOH / CH₂Cl₂; methanol / 2 h / -10 - 10 °C

11: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h

12: amonium formate, Pd₂(dba)3*CHCl₃, tributylphosphine / dioxane / 1 h / Heating

13: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,

14: 1.) 1,7 M tert-butyllithium / 1.) THF, pentane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

With 4-methyl-morpholine; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; N-Bromosuccinimide; tetrapropylammonium perruthennate; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; methyllithium; dihydrogen peroxide; tert.-butyl lithium; ammonium formate; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja9533454

Reference yield:

: 172996-05-3
methyl (1S,3aR,6R,6aR)-6-(1,1-dimethoxyethyl)octahydro-3-oxo-1-pentalenecarboxylate

: 172996-24-6
(3S,3aR,5aR,7aS,7bR)-7a-Benzyloxy-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-cyclopent-1-enyl]-3-methyl-6-methylene-octahydro-pentaleno[1,6-cd]pyran-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: LDA / tetrahydrofuran

2: NBS, propylene oxide, Et₃N

3: 78 percent / 30percent H₂O₂, 1 N NaOH / CH₂Cl₂; methanol / 2 h / -10 - 10 °C

4: 1). 1.3 M n-butyllithium / 1). THF, RT, 0.5 h, 2). THF, from -78 deg C to RT, 6 h

5: amonium formate, Pd₂(dba)3*CHCl₃, tributylphosphine / dioxane / 1 h / Heating

6: 1.) tetrabutylammonium iodide, sodium hydride, 2.) p-toluenosulfonic acid / 1.) DMF, 15 min., 2.) acetone, 5 min.,

7: 1.) 1,7 M tert-butyllithium / 1.) THF, pentane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; N-Bromosuccinimide; tributylphosphine; dihydrogen peroxide; tert.-butyl lithium; ammonium formate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; methyloxirane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/ja9533454