(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

Base Information

Chemical Name:(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane
CAS No.:132514-46-6
Molecular Formula:C₂₃H₃₆O₃Si
Molecular Weight:388.623
Hs Code.:

Synonyms:(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

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Chemical Property of (R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

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Technology Process of (R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

There total 13 articles about (R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane 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:

: 876-53-9
1,3-dibromoadamantane

: 132514-46-6
(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 8 steps

1: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C

2: 1.) BF₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min

3: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight

4: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

6: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

7: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

8: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; dihydrogen peroxide; lithium triethylborohydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042

Reference yield:

: 768-90-1
1-Adamantyl bromide

: 132514-46-6
(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / Br₂, AlBr₃, BBr₃ / 1.5 h / 85 °C

2: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C

3: 1.) BF₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min

4: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight

5: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

7: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

8: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

9: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; aluminum tri-bromide; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; dihydrogen peroxide; bromine; boron tribromide; lithium triethylborohydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042

Reference yield:

: 281-23-2
adamantane

: 132514-46-6
(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-<<(tert-butyldimethylsilyl)oxy>methyl>bicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / Br₂ / 2 h / 105 °C

2: 87 percent / Br₂, AlBr₃, BBr₃ / 1.5 h / 85 °C

3: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C

4: 1.) BF₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min

5: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight

6: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

7: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

8: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

9: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

10: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; aluminum tri-bromide; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; dihydrogen peroxide; bromine; boron tribromide; lithium triethylborohydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042