1(2H)-Pyridinecarboxylic acid, 3-butyl-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(tri fluoromethyl)sulfonyl]oxy]-, methyl ester, (2S,3R)-

Base Information

• Chemical Name: 1(2H)-Pyridinecarboxylic acid, 3-butyl-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(tri fluoromethyl)sulfonyl]oxy]-, methyl ester, (2S,3R)-
• CAS No.: 847358-34-3
• Molecular Formula: C29H38F3NO6SSi
• Molecular Weight: 613.771

Synonyms:

Chemical Property of 1(2H)-Pyridinecarboxylic acid, 3-butyl-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(tri fluoromethyl)sulfonyl]oxy]-, methyl ester, (2S,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1(2H)-Pyridinecarboxylic acid, 3-butyl-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(tri fluoromethyl)sulfonyl]oxy]-, methyl ester, (2S,3R)-

There total 11 articles about 1(2H)-Pyridinecarboxylic acid, 3-butyl-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3,4-dihydro-6-[[(tri fluoromethyl)sulfonyl]oxy]-, methyl ester, (2S,3R)- 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:

(R)-(+)-propionic acid 2-(hydroxymethyl)hexyl ester (847358-25-2) → (2S,3R)-(-)-3-butyl-2-(tert-butyldiphenylsilanyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydropyridine-1(2H)-carboxylic acid methyl ester (847358-34-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: PPTS / CH₂Cl₂ / 6 h / 20 °C

2.1: MeOH; K₂CO₃ / 19 h / 20 °C

3.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: tetrahydrofuran; hexane / 22 h / 20 °C

5.1: (DHQD)2PYR; K₃Fe(CN)6; K₂CO₃ / K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 17 h / 0 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 45 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

8.1: NaN₃ / dimethylformamide / 15 h / 80 °C

9.1: PPTS; EtOH / 2 h / 60 °C

10.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

11.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

11.2: tetrahydrofuran / 2 h / 20 °C

12.1: hydrogen / Pd/C / ethyl acetate / 48 h / 3040 Torr

13.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

14.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

14.2: tetrahydrofuran; hexane / 0.5 h / -78 - -40 °C

With methanol; dmap; n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; ethanol; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; potassium hexacyanoferrate(III); potassium osmate(VI); palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Wittig reaction / 5.1: Sharpless asymmetric dihydroxylation / 10.1: Swern oxidation / 11.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.11.060

Reference yield:

(R)-2-(Tetrahydro-pyran-2-yloxymethyl)-hexanal → (2S,3R)-(-)-3-butyl-2-(tert-butyldiphenylsilanyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydropyridine-1(2H)-carboxylic acid methyl ester (847358-34-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: tetrahydrofuran; hexane / 22 h / 20 °C

2.1: (DHQD)2PYR; K₃Fe(CN)6; K₂CO₃ / K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 17 h / 0 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 45 h / 20 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: NaN₃ / dimethylformamide / 15 h / 80 °C

6.1: PPTS; EtOH / 2 h / 60 °C

7.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

8.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

8.2: tetrahydrofuran / 2 h / 20 °C

9.1: hydrogen / Pd/C / ethyl acetate / 48 h / 3040 Torr

10.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

11.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.2: tetrahydrofuran; hexane / 0.5 h / -78 - -40 °C

With dmap; n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; ethanol; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; potassium hexacyanoferrate(III); potassium osmate(VI); palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1.2: Wittig reaction / 2.1: Sharpless asymmetric dihydroxylation / 7.1: Swern oxidation / 8.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.11.060

Reference yield:

(S)-(+)-2-(2-butylbut-3-enyloxy)tetrahydropyran (847358-28-5) → (2S,3R)-(-)-3-butyl-2-(tert-butyldiphenylsilanyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydropyridine-1(2H)-carboxylic acid methyl ester (847358-34-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (DHQD)2PYR; K₃Fe(CN)6; K₂CO₃ / K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 17 h / 0 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 45 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: NaN₃ / dimethylformamide / 15 h / 80 °C

5.1: PPTS; EtOH / 2 h / 60 °C

6.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

7.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

7.2: tetrahydrofuran / 2 h / 20 °C

8.1: hydrogen / Pd/C / ethyl acetate / 48 h / 3040 Torr

9.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

10.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: tetrahydrofuran; hexane / 0.5 h / -78 - -40 °C

With dmap; n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; ethanol; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; potassium hexacyanoferrate(III); potassium osmate(VI); palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2004.11.060

upstream raw materials:

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

(2S,3R)-3-Butyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-oxo-piperidine-1-carboxylic acid methyl ester

(R)-(+)-propionic acid 2-(hydroxymethyl)hexyl ester

(S)-(+)-2-(2-butylbut-3-enyloxy)tetrahydropyran

Downstream raw materials:

(2S,3R)-(-)-6-allyl-3-butyl-2-(tert-butyldiphenylsilanyloxymethyl)-3,4-dihydropyridine-1(2H)-carboxylic acid methyl ester

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