(1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane

Base Information

• Chemical Name: (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane
• CAS No.: 130607-96-4
• Molecular Formula: C₁₇H₃₃NOSi
• Molecular Weight: 295.541

Synonyms:

Chemical Property of (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane

There total 12 articles about (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane 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) → (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane (124908-76-5,130607-96-4,142560-65-4)

Guidance literature:

Multi-step reaction with 10 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

8: 72 percent / H₂ / 10percent Pd/C / ethanol

9: ethanol / 1.5 h / Heating

10: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

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; hydrogen; sodium methylate; sodium acetate; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester → (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane (124908-76-5,130607-96-4,142560-65-4)

Guidance literature:

Multi-step reaction with 11 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

9: 72 percent / H₂ / 10percent Pd/C / ethanol

10: ethanol / 1.5 h / Heating

11: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

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; hydrogen; sodium methylate; sodium acetate; diisobutylaluminium hydride; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

3-<<(tert-Butyldimethylsilyl)oxy>methyl>-1-methoxy-5-methyl-1,4-cyclohexadiene (124908-72-1) → (1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane (124908-76-5,130607-96-4,142560-65-4)

Guidance literature:

Multi-step reaction with 9 steps

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

2: 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)

3: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

4: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

5: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

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

7: 72 percent / H₂ / 10percent Pd/C / ethanol

8: ethanol / 1.5 h / Heating

9: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

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; hydrogen; sodium methylate; sodium acetate; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/jo00036a026

upstream raw materials:

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

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

3-<<(tert-Butyldimethylsilyl)oxy>methyl>-1-methoxy-5-methyl-1,4-cyclohexadiene

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

Downstream raw materials:

(S)-2-((1R,2S,6R)-2-Hydroxymethyl-6-methyl-cyclohexyl)-propionitrile

(S)-2-((1R,2S,6R)-2-Formyl-6-methyl-cyclohexyl)-propionitrile

(E)-2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2S,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-acrylic acid methyl ester

(Z)-2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-yl]-3-[(1S,2S,3R)-2-((S)-cyano-methyl-methyl)-3-methyl-cyclohexyl]-acrylic acid methyl ester

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