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

Base Information

• Chemical Name: {(2R,3S)-2-{(1R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester
• CAS No.: 181464-29-9
• Molecular Formula: C₃₀H₅₃NO₈Si₂
• Molecular Weight: 611.924

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

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

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

There total 4 articles about {(2R,3S)-2-{(1R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-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: 100.0%

allyl oxalyl chloride (74503-07-4) + (3S,4R)-4-{(1R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (144572-86-1) → {(2R,3S)-2-{(1R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester (181464-29-9)

Guidance literature:

With TEA; potassium carbonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/0960-894X(96)00358-7

Reference yield:

(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (135297-04-0) → {(2R,3S)-2-{(1R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester (181464-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pTSA / CH₂Cl₂

2: imidazole / dimethylformamide

3: 1) DMSO, (COCl)2, 2) TEA / 1) CH₂Cl₂, -78 deg C

4: TEA / CH₂Cl₂

With 1H-imidazole; oxalyl dichloride; TEA; toluene-4-sulfonic acid; dimethyl sulfoxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00359-9

Reference yield:

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1R,2S,3S)-2-hydroxy-3-(2-hydroxy-ethoxy)-cyclohexyl]-azetidin-2-one (181421-47-6) → {(2R,3S)-2-{(1R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester (181464-29-9)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide

2: 1) DMSO, (COCl)2, 2) TEA / 1) CH₂Cl₂, -78 deg C

3: TEA / CH₂Cl₂

With 1H-imidazole; oxalyl dichloride; TEA; dimethyl sulfoxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0960-894X(96)00359-9

upstream raw materials:

allyl oxalyl chloride

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

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

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

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