(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

Base Information

Chemical Name:(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one
CAS No.:528821-13-8
Molecular Formula:C₂₆H₃₅NO₃Si
Molecular Weight:437.654
Hs Code.:

Synonyms:(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

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Chemical Property of (5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

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Technology Process of (5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

There total 5 articles about (5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-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: 64.0%

: 100-39-0
benzyl bromide

: 528821-08-1
(5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-1H-pyridin-2-one

: 528821-13-8
(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

Guidance literature:: (5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-1H-pyridin-2-one; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)01534-X

Reference yield:

: 124085-68-3
tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate

: 528821-13-8
(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / -78 - 20 °C

2.1: 7.23 g / potassium tert-butoxide / tetrahydrofuran / 3 h / 20 °C

3.1: 81 percent / PdCl₂(PPh₃)2 / ethanol / 32 h / 60 °C / 45600 Torr

4.1: 76 percent / NaHCO₃; Oxone / acetone; H₂O / 3 h / 20 °C

5.1: 95 percent / DBU / CH₂Cl₂ / 3 h / Heating

6.1: NaH / dimethylformamide / 0.5 h / 0 °C

6.2: 64 percent / dimethylformamide / 0 - 20 °C

With bis-triphenylphosphine-palladium(II) chloride; Oxone; potassium tert-butylate; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(02)01534-X

Reference yield:

: 736143-67-2
(4R)-4-[(tert-butyldimethylsilanyloxy)methyl]-5-vinyl-1,3-oxazolidine-2-one

: 528821-13-8
(5S,6R)-1-benzyl-5-benzyloxy-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-1H-pyridin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / PdCl₂(PPh₃)2 / ethanol / 32 h / 60 °C / 45600 Torr

2.1: 76 percent / NaHCO₃; Oxone / acetone; H₂O / 3 h / 20 °C

3.1: 95 percent / DBU / CH₂Cl₂ / 3 h / Heating

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 64 percent / dimethylformamide / 0 - 20 °C

With bis-triphenylphosphine-palladium(II) chloride; Oxone; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(02)01534-X