(2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

Base Information

Chemical Name:(2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one
CAS No.:258531-65-6
Molecular Formula:C₃₁H₃₇NO₅SSi
Molecular Weight:563.79
Hs Code.:

Synonyms:(2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

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Chemical Property of (2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

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Technology Process of (2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

There total 8 articles about (2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-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: 81.0%

: 122-51-0
orthoformic acid triethyl ester

: 249928-45-8
(2S,6S)-2-(tert-Butyldiphenylsilyloxymethyl)-6-hydroxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

: 258531-65-6
(2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1055/s-1999-3604

Reference yield:

: 14086-08-9
(R)-2-(2-furyl)-1,2-ethanediol

: 258531-65-6
(2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole; DMAP / dimethylformamide

2: 84 percent / DPPA; DBU / toluene / 22 h / 0 - 20 °C

3: H₂ / 10 percent Pd/C / methanol / 0.67 h / 750.06 Torr

4: Et₃N / CH₂Cl₂ / 3 h / 20 °C

5: 91 percent / MCPBA / CH₂Cl₂ / 3 h

6: 81 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Esterification / 2: Substitution / 3: Catalytic hydrogenation / 4: Tosylation / 5: Rearrangement / 6: Etherification;
DOI:10.1055/s-1999-3604

Reference yield:

: 124067-17-0
(2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol

: 258531-65-6
(2S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / DPPA; DBU / toluene / 22 h / 0 - 20 °C

2: H₂ / 10 percent Pd/C / methanol / 0.67 h / 750.06 Torr

3: Et₃N / CH₂Cl₂ / 3 h / 20 °C

4: 91 percent / MCPBA / CH₂Cl₂ / 3 h

5: 81 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / tetrahydrofuran / 3 h / 0 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Substitution / 2: Catalytic hydrogenation / 3: Tosylation / 4: Rearrangement / 5: Etherification;
DOI:10.1055/s-1999-3604