6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 883142-62-9
• Molecular Formula: C₂₉H₃₉NO₅Si
• Molecular Weight: 509.718

Synonyms:6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester

Chemical Property of 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester

There total 15 articles about 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl 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: 81.0%

2-(tert-butyl-diphenyl-silanyloxymethyl)-3-propyl-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester (1025941-03-0) + methanol (67-56-1) + carbon monoxide (201230-82-2) → 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester (883142-62-9)

Guidance literature:

With triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 75 ℃;

DOI:10.1055/s-2005-921911

Reference yield:

(R)-2-(Tetrahydro-pyran-2-yloxymethyl)-pentanal → 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester (883142-62-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-BuLi

1.2: tetrahydrofuran / 0 - 20 °C

2.1: (DHQD)2PYR; K₂OsO₄; aq. K₂CO₃ / K₃Fe(CN)6 / 2-methyl-propan-2-ol / 0 h

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 0 °C

5.1: NaN₃ / dimethylformamide / 80 °C

6.1: PPTS / ethanol / 60 °C

7.1: NaH / tetrahydrofuran / 0 - 20 °C

8.1: 60 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

9.1: LiHMDS / tetrahydrofuran

9.2: 94 percent / tetrahydrofuran / -78 - -40 °C

10.1: 81 percent / Et₃N / Pd(Ph₃P)4 / dimethylformamide / 75 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexacyanoferrate(III); In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation / 7.1: Swern oxidation / 8.1: Horner-Emmons reaction;

DOI:10.1055/s-2005-921911

Reference yield:

2-(2-propyl-but-3-enyloxy)-tetrahydro-pyran (883142-56-1) → 6-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylic acid dimethyl ester (883142-62-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (DHQD)2PYR; K₂OsO₄; aq. K₂CO₃ / K₃Fe(CN)6 / 2-methyl-propan-2-ol / 0 h

2.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: Et₃N / CH₂Cl₂ / 0 °C

4.1: NaN₃ / dimethylformamide / 80 °C

5.1: PPTS / ethanol / 60 °C

6.1: NaH / tetrahydrofuran / 0 - 20 °C

7.1: 60 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

8.1: LiHMDS / tetrahydrofuran

8.2: 94 percent / tetrahydrofuran / -78 - -40 °C

9.1: 81 percent / Et₃N / Pd(Ph₃P)4 / dimethylformamide / 75 °C

With dmap; potassium osmate(VI); sodium azide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexacyanoferrate(III); In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 6.1: Swern oxidation / 7.1: Horner-Emmons reaction;

DOI:10.1055/s-2005-921911

upstream raw materials:

2-(tert-butyl-diphenyl-silanyloxymethyl)-3-propyl-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester

methanol

carbon monoxide

2-(2-propyl-but-3-enyloxy)-tetrahydro-pyran

Downstream raw materials:

(2R,3S,5R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-propyl-3-vinyl-piperidine-1,2-dicarboxylic acid dimethyl ester

(2S,3R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-ethyl-6-(3-hydroxy-propyl)-3-propyl-piperidine-1-carboxylic acid methyl ester

(2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester

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