[(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-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-(di-tert-butyl-hydroxy-silanyloxy)-cyclohexyloxy]-acetic acid allyl ester
• CAS No.: 198402-06-1
• Molecular Formula: C₃₀H₅₇NO₇Si₂
• Molecular Weight: 599.956

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about [(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-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: 15.0%

allyl alcohol (107-18-6) + {(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 ethyl ester (198402-04-9) → {(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 (198402-05-0) + [(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-cyclohexyloxy]-acetic acid allyl ester (198402-06-1)

Guidance literature:

With potassium tert-butylate; for 2h; -20 deg C -> room temperature;

DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

di-tert-butylsilyl bis(trifluoromethanesulfonate) (85272-31-7) → [(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-cyclohexyloxy]-acetic acid allyl ester (198402-06-1)

Guidance literature:

Multi-step reaction with 4 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: 15 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

With 2,6-dimethylpyridine; dirhodium tetraacetate; potassium tert-butylate; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (135297-04-0) → [(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-cyclohexyloxy]-acetic acid allyl ester (198402-06-1)

Guidance literature:

Multi-step reaction with 5 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: 15 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

With 2,6-dimethylpyridine; dirhodium tetraacetate; ammonium cerium(IV) nitrate; potassium tert-butylate; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(97)01053-3

upstream raw materials:

allyl alcohol

{(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 ethyl ester

di-tert-butylsilyl bis(trifluoromethanesulfonate)

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

Downstream raw materials:

((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

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

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

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

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