5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester
• CAS No.: 930093-51-9
• Molecular Formula: C₂₈H₃₉NO₆Si
• Molecular Weight: 513.706

Synonyms:5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester

Chemical Property of 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester

There total 14 articles about 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester 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: 60.0%

5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester → 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester (930093-51-9)

Guidance literature:

With Bromotrichloromethane; N,N,N',N'-tetramethylguanidine; In dichloromethane; at 22 ℃;

DOI:10.3987/com-05-s(t)70

Reference yield:

(R)-2-cyclohexen-1-ol (3413-44-3) → 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester (930093-51-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 84 percent / imidazole / CH₂Cl₂

2.1: m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 0 °C

3.1: [C(CH₃)2(CH₂)3C(CH₃)2]NLi / hexane; benzene / 0 - 20 °C

4.1: 87 percent / tri-n-butylphosphine / CH₂Cl₂ / 0.08 h / 22 °C

5.1: 86 percent / DIBAL / toluene

6.1: 97 percent / imidazole / CH₂Cl₂

7.1: toluene / 180 °C

8.1: PPTs; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

8.2: NaCNBH₃ / acetic acid / 10 °C

9.1: 75 percent / benzotriazol-1-yloxytris(Me₂N)phosphonium hexaFphosphate

10.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

11.1: 60 percent / BrCCl₃; (Me₂N)2C=NH / CH₂Cl₂ / 22 °C

With 1H-imidazole; oxalyl dichloride; Bromotrichloromethane; tributylphosphine; 4 A molecular sieve; 2,2,6,6-tetramethylpiperidinyl-lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N,N',N'-tetramethylguanidine; In hexane; dichloromethane; toluene; benzene; 10.1: Swern oxidation;

DOI:10.3987/com-05-s(t)70

Reference yield:

tert-butyl-(cyclohex-2-enyloxy)-dimethyl-silane (882175-52-2) → 5-[(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-1-(4-methoxy-benzyloxy)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid ethyl ester (930093-51-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 0 °C

2.1: [C(CH₃)2(CH₂)3C(CH₃)2]NLi / hexane; benzene / 0 - 20 °C

3.1: 87 percent / tri-n-butylphosphine / CH₂Cl₂ / 0.08 h / 22 °C

4.1: 86 percent / DIBAL / toluene

5.1: 97 percent / imidazole / CH₂Cl₂

6.1: toluene / 180 °C

7.1: PPTs; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

7.2: NaCNBH₃ / acetic acid / 10 °C

8.1: 75 percent / benzotriazol-1-yloxytris(Me₂N)phosphonium hexaFphosphate

9.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

10.1: 60 percent / BrCCl₃; (Me₂N)2C=NH / CH₂Cl₂ / 22 °C

With 1H-imidazole; oxalyl dichloride; Bromotrichloromethane; tributylphosphine; 4 A molecular sieve; 2,2,6,6-tetramethylpiperidinyl-lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N,N',N'-tetramethylguanidine; In hexane; dichloromethane; toluene; benzene; 9.1: Swern oxidation;

DOI:10.3987/com-05-s(t)70

upstream raw materials:

tert-butyl-(cyclohex-2-enyloxy)-dimethyl-silane

(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enol

(1α,2α,6α)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-oxa-bicyclo[4.1.0]heptane

(E)-3-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyloxy]-prop-2-en-1-ol

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