(3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one
• CAS No.: 135297-25-5
• Molecular Formula: C₁₇H₃₀N₄O₃Si
• Molecular Weight: 366.536

Synonyms:(3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Chemical Property of (3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Chemical Property:

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Technology Process of (3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

There total 1 articles about (3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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: 70.0%

(3S,4R)-4-((1R,2S,3S)-3-Azido-2-hydroxy-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (181228-86-4) → (3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (135297-25-5)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 22 ℃; for 18h;

DOI:10.1016/0960-894X(96)00292-2

Reference yield:

(3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (135297-25-5) → (3S,4R)-4-((1R,3S)-3-Amino-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 22 ℃; for 5h; under 2280 Torr;

DOI:10.1016/0960-894X(96)00292-2

Reference yield:

(3S,4R)-4-((1R,3S)-3-Azido-2-oxo-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (135297-25-5) → ((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-carbamic acid allyl ester (135297-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate / 5 h / 22 °C / 2280 Torr

2: triethylamine; CH₂Cl₂ / 0.17 h / 0 °C

With hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate; triethylamine;

DOI:10.1016/0960-894X(96)00292-2

upstream raw materials:

(3S,4R)-4-((1R,2S,3S)-3-Azido-2-hydroxy-cyclohexyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Downstream raw materials:

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

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