(+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

Base Information

Chemical Name:(+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone
CAS No.:614733-36-7
Molecular Formula:C₂₉H₃₅NO₃Si
Molecular Weight:473.687
Hs Code.:

Synonyms:(+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

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Chemical Property of (+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

Chemical Property:

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Technology Process of (+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

There total 10 articles about (+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone 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:

: 148968-08-5
(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

: 614733-36-7
(+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

Guidance literature:: Multi-step reaction with 11 steps

1: Me₂NH / H₂O; benzene / 48 h / 20 °C

2: NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

3: 90 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 24 h / 20 °C

4: 72 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

5: 92 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

6: 95 percent / LiAlH₄ / tetrahydrofuran / 1.33 h / 0 °C

7: 95 percent / 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

8: methanol / 12 h / 20 °C

9: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

10: 4-(dimethylamino)pyridine / toluene / 1 h / Heating

11: 92 percent / H₂ / Pd/C / ethyl acetate / 1 h

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; dimethyl amine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

: 160334-80-5
(-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone

: 614733-36-7
(+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

Guidance literature:: Multi-step reaction with 10 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

2: 90 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 24 h / 20 °C

3: 72 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

4: 92 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

5: 95 percent / LiAlH₄ / tetrahydrofuran / 1.33 h / 0 °C

6: 95 percent / 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

7: methanol / 12 h / 20 °C

8: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

9: 4-(dimethylamino)pyridine / toluene / 1 h / Heating

10: 92 percent / H₂ / Pd/C / ethyl acetate / 1 h

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

: 614733-26-5
(+)-(3R,4R)-3-benzyloxy-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-azetidinone

: 614733-36-7
(+)-(5S,6R)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-pyridinone

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

2: 95 percent / LiAlH₄ / tetrahydrofuran / 1.33 h / 0 °C

3: 95 percent / 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

4: methanol / 12 h / 20 °C

5: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6: 4-(dimethylamino)pyridine / toluene / 1 h / Heating

7: 92 percent / H₂ / Pd/C / ethyl acetate / 1 h

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/S0040-4020(03)01063-9