(5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

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Chemical Name:(5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one
CAS No.:479411-09-1
Molecular Formula:C₂₆H₃₅NO₅SSi
Molecular Weight:501.719
Hs Code.:

Synonyms:(5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

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Chemical Property of (5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

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Technology Process of (5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

There total 10 articles about (5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-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: 93.0%

: 475976-13-7
(2S,3S,6R)-3-benzyloxy-2-(tert-butyl-dimethyl-siloxymethyl)-6-methoxy-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridine

: 479411-09-1
(5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: 222986-35-8
(1R)-2-[(tert-butyldimethylsilyl)oxy]-1-(furan-2-yl)ethanol

: 479411-09-1
(5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 80 percent / diphenylphosphorazide; DBU / toluene / 10 h

2.1: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr

3.1: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

4.1: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

5.1: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C

6.1: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

7.1: sodium hydride / tetrahydrofuran / 0.5 h

7.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h

8.1: 93 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: (S)-(2-azido-2-furan-2-yl-ethoxy)-tert-butyl-dimethyl-silane

: 479411-09-1
(5S,6S)-5-benzyloxy-6-(tert-butyl-dimethyl-siloxymethyl)-1-(toluene-4-sulfonyl)-5,6-dihydro-1H-pyridine-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr

2.1: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

3.1: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

4.1: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C

5.1: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

6.1: sodium hydride / tetrahydrofuran / 0.5 h

6.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h

7.1: 93 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(02)00674-9