(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

Base Information

Chemical Name:(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate
CAS No.:262375-53-1
Molecular Formula:C₃₃H₅₈O₅Si₂
Molecular Weight:590.992
Hs Code.:

Synonyms:(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

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Chemical Property of (3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

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Technology Process of (3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

There total 12 articles about (3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate 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:

: 2-Methyl-2-[(4R,5R,6S)-2,2,5-trimethyl-6-((S)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-propionaldehyde

: 262375-53-1
(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium bis(trimethylsilyl)amide; H₂O / (R)-LaLi₃tris(binaphthoxide) / toluene; tetrahydrofuran / 0.33 h / -20 °C

1.2: toluene; H₂O; tetrahydrofuran / 168 h / -20 °C

2.1: K₂CO₃; SnCl₄; bis(trimethylsilyl)peroxide / trans-1,2-bisNHTs-cyclohexane; MS 4A / CH₂Cl₂ / 10 h / 0 °C

3.1: BCl₃ / CH₂Cl₂; xylene / 0.33 h / -78 °C

4.1: diisopropylethylamine / CH₂Cl₂ / 0.5 h

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With bis-trimethylsilanyl peroxide; water; boron trichloride; tin(IV) chloride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; (R)-LaLi₃tris(binaphthoxide); In tetrahydrofuran; dichloromethane; toluene; xylene; 2.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja002024b

Reference yield:

: (4S,5R)-7-Benzyloxy-5-hydroxy-4,6,6-trimethyl-heptan-3-one

: 262375-53-1
(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; LHMDS / tetrahydrofuran / 0.67 h / -78 °C

1.2: 48 percent / tetrahydrofuran / 1.5 h / -78 °C

2.1: 79 percent / Me₄NBH(OAc)3; AcOH / acetonitrile

3.1: 96 percent / TsOH / dimethylformamide

4.1: 100 percent / Li; liq. NH₃ / 2-methyl-propan-2-ol; tetrahydrofuran

5.1: 89 percent / TPAP; NMO; molecular sieves 4 A / CH₂Cl₂

6.1: potassium bis(trimethylsilyl)amide; H₂O / (R)-LaLi₃tris(binaphthoxide) / toluene; tetrahydrofuran / 0.33 h / -20 °C

6.2: toluene; H₂O; tetrahydrofuran / 168 h / -20 °C

7.1: K₂CO₃; SnCl₄; bis(trimethylsilyl)peroxide / trans-1,2-bisNHTs-cyclohexane; MS 4A / CH₂Cl₂ / 10 h / 0 °C

8.1: BCl₃ / CH₂Cl₂; xylene / 0.33 h / -78 °C

9.1: diisopropylethylamine / CH₂Cl₂ / 0.5 h

10.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-methyl-2-indolinone; tetrapropylammonium perruthennate; bis-trimethylsilanyl peroxide; 4 A molecular sieve; ammonia; water; boron trichloride; tin(IV) chloride; lithium; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; (R)-LaLi₃tris(binaphthoxide); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; xylene; tert-butyl alcohol; 4.1: Birch reduction / 7.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja002024b

Reference yield:

: 2-Methyl-2-[(4R,5R,6S)-2,2,5-trimethyl-6-((S)-1-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-propan-1-ol

: 262375-53-1
(3S,6R,7S,8S)-phenyl 3,7-di-tert-butyldimethylsilyloxy-4,4,6,8-tetramethyl-5-oxo-10-undecenoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / TPAP; NMO; molecular sieves 4 A / CH₂Cl₂

2.1: potassium bis(trimethylsilyl)amide; H₂O / (R)-LaLi₃tris(binaphthoxide) / toluene; tetrahydrofuran / 0.33 h / -20 °C

2.2: toluene; H₂O; tetrahydrofuran / 168 h / -20 °C

3.1: K₂CO₃; SnCl₄; bis(trimethylsilyl)peroxide / trans-1,2-bisNHTs-cyclohexane; MS 4A / CH₂Cl₂ / 10 h / 0 °C

4.1: BCl₃ / CH₂Cl₂; xylene / 0.33 h / -78 °C

5.1: diisopropylethylamine / CH₂Cl₂ / 0.5 h

6.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; bis-trimethylsilanyl peroxide; 4 A molecular sieve; water; boron trichloride; tin(IV) chloride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; racemic trans-N,N'-bis(p-toluenesulfonyl)cyclohexane-1,2-diamine; (R)-LaLi₃tris(binaphthoxide); In tetrahydrofuran; dichloromethane; toluene; xylene; 3.1: Baeyer-Villiger oxidation;
DOI:10.1021/ja002024b