2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide

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Chemical Name:2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide
CAS No.:198402-17-4
Molecular Formula:C₂₁H₃₈N₂O₅Si
Molecular Weight:426.629
Hs Code.:

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Chemical Property of 2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide

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Technology Process of 2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide

There total 10 articles about 2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide 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: 40.0%

: 198402-16-3
2-((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-N,N-dimethyl-acetamide

: 198402-17-4
2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h;
DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

: 135297-04-0
(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

: 198402-17-4
2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 11 steps

1: 53 percent / ceric ammonium nitrate / acetonitrile / 20 h / Ambient temperature

2: 79 percent / 2,6-lutidine / CH₂Cl₂ / 5 °C

3: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

4: 72 percent / 2(OAc)>4 / CH₂Cl₂ / 6 h / Ambient temperature

5: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

6: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

7: 1.) 2,6-lutidine, 2.) Pd(PPh₃)4, sodium 2-ethylhexanoate, buffer pH=3 / 1.) CH₂Cl₂

8: PPh₃ / CH₂Cl₂

9: CH₂Cl₂ / 1 h

10: 75 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 1 h

11: 40 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; ammonium cerium(IV) nitrate; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

: 190973-56-9
(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,2S,3S)-2-hydroxy-3-nitrooxy-cyclohexyl)-azetidin-2-one

: 198402-17-4
2-((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 10 steps

1: 79 percent / 2,6-lutidine / CH₂Cl₂ / 5 °C

2: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

3: 72 percent / 2(OAc)>4 / CH₂Cl₂ / 6 h / Ambient temperature

4: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

5: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

6: 1.) 2,6-lutidine, 2.) Pd(PPh₃)4, sodium 2-ethylhexanoate, buffer pH=3 / 1.) CH₂Cl₂

7: PPh₃ / CH₂Cl₂

8: CH₂Cl₂ / 1 h

9: 75 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 1 h

10: 40 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(97)01053-3