(4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one

Base Information

• Chemical Name: (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one
• CAS No.: 142560-63-2
• Molecular Formula: C₁₇H₂₉NO₂Si
• Molecular Weight: 307.508
• Mol file: 142560-63-2.mol

Synonyms:(4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one

Chemical Property of (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one

There total 8 articles about (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-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:

(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol (142459-32-3) → (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one (142560-63-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

2: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

3: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

4: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

6: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

7: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; sodium methylate; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; In dichloromethane; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid (124908-71-0) → (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one (142560-63-2)

Guidance literature:

Multi-step reaction with 9 steps

1: diethyl ether

2: 8.28 g / DIBALH / hexane; diethyl ether / 1.5 h / -50 °C

3: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

4: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

5: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

6: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

7: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

8: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

9: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; sodium methylate; diisobutylaluminium hydride; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; In diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester → (4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one (142560-63-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 8.28 g / DIBALH / hexane; diethyl ether / 1.5 h / -50 °C

2: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

3: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

4: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

5: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

6: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

7: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

8: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; sodium methylate; diisobutylaluminium hydride; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; In diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo00036a026

upstream raw materials:

(1S,3R,4S,8R)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-bicyclo[2.2.2]oct-5-en-2-one oxime

(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid

(1S,3R,4R,8R)-8-<<(tert-Butyldimethylsilyl)oxy>-methyl>-1-methoxy-3,5-dimethylbicyclo<2.2.2>oct-5-en-2-one

Downstream raw materials:

(Z)-3-[(1R,2R,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

(E)-3-[(1R,2R,3S)-2-((R)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester

C₄₁H₆₈O₈Si

4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one