((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

Base Information

Chemical Name:((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester
CAS No.:198402-07-2
Molecular Formula:C₂₂H₃₉NO₆Si
Molecular Weight:441.64
Hs Code.:

Synonyms:((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

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Chemical Property of ((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

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Technology Process of ((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

There total 7 articles about ((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester 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: 55.0%

: 198402-05-0
{(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-5-yloxy}-acetic acid allyl ester

: 198402-07-2
((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 2h; Ambient temperature;
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

: 198402-07-2
((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

Guidance literature:: Multi-step reaction with 6 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

With 2,6-dimethylpyridine; dirhodium tetraacetate; ammonium cerium(IV) nitrate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

: 190973-58-1
(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-nitrooxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

: 198402-07-2
((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

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

3: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

4: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

With dirhodium tetraacetate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(97)01053-3