(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

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Chemical Name:(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one
CAS No.:93576-40-0
Molecular Formula:C₂₃H₃₄N₂O₇Si
Molecular Weight:478.618
Hs Code.:

Synonyms:(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

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Chemical Property of (3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

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Technology Process of (3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

There total 9 articles about (3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-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:

: 102831-99-2
(4S)-1-(tert-Butyldimethylsilyl)-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one

: 93576-40-0
(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 4 h / Ambient temperature

2: 10 percent citric acid / tetrahydrofuran / 2 h / Ambient temperature

3: 1) lithiumdiisopropylamide (LDA) / 1) THF, -40 deg C, 15 min., 2) THF, r.t., 15 min.

4: 71 percent / 1) 1M Mg(CF₃COO)2, 2) (i-Pr)2NH*BH₃ / diethyl ether / 1) -78 deg C, 20 min., 2) -78 deg C, 1 h

5: 1) 1,1'-carbonyldiimidazole / 1) MeCN, r.t., 0.5 h, 2) 50 deg C, 18 h

With diisopropylamine borane; magnesium(II) 2,2,2-trifluoroacetate; 1,1'-carbonyldiimidazole; citric acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;
DOI:10.1021/jo00041a031

Reference yield:

: 102831-94-7
(4S)-4-<(1R)-1-<((4S)-4-Ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one

: 93576-40-0
(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / Et₃N / dimethylformamide / 0.5 h / 0 °C

2: tetrahydrofuran / 4 h / Ambient temperature

3: 10 percent citric acid / tetrahydrofuran / 2 h / Ambient temperature

4: 1) lithiumdiisopropylamide (LDA) / 1) THF, -40 deg C, 15 min., 2) THF, r.t., 15 min.

5: 71 percent / 1) 1M Mg(CF₃COO)2, 2) (i-Pr)2NH*BH₃ / diethyl ether / 1) -78 deg C, 20 min., 2) -78 deg C, 1 h

6: 1) 1,1'-carbonyldiimidazole / 1) MeCN, r.t., 0.5 h, 2) 50 deg C, 18 h

With diisopropylamine borane; magnesium(II) 2,2,2-trifluoroacetate; triethylamine; 1,1'-carbonyldiimidazole; citric acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo00041a031

Reference yield:

: 102832-01-9
(4S)-4-<(1R)-1-(benzyloxycarbonyl)ethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine

: 93576-40-0
(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / H₂ / 5percent Pd / C / methanol / 14 h / Ambient temperature

2: 1) lithiumdiisopropylamide (LDA) / 1) THF, -40 deg C, 15 min., 2) THF, r.t., 15 min.

3: 71 percent / 1) 1M Mg(CF₃COO)2, 2) (i-Pr)2NH*BH₃ / diethyl ether / 1) -78 deg C, 20 min., 2) -78 deg C, 1 h

4: 1) 1,1'-carbonyldiimidazole / 1) MeCN, r.t., 0.5 h, 2) 50 deg C, 18 h

With diisopropylamine borane; hydrogen; magnesium(II) 2,2,2-trifluoroacetate; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; palladium; In methanol; diethyl ether;
DOI:10.1021/jo00041a031