(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one
• CAS No.: 184531-16-6
• Molecular Formula: C₂₇H₄₃N₂O₅PSi
• Molecular Weight: 534.708

Synonyms:(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one

Chemical Property of (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one

There total 19 articles about (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-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: 72.0%

(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one (184531-14-4) → (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one (184531-16-6)

Guidance literature:

With potassium fluoride; In methanol; for 1.5h;

DOI:10.1016/0957-4166(96)00384-9

Reference yield:

cis-ethyl 2-hydroxy-cyclohexanoate (1655-06-7,3444-72-2,6125-55-9,6149-52-6,29569-79-7,61586-78-5,77026-73-4,119068-36-9,119068-37-0) → (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one (184531-16-6)

Guidance literature:

Multi-step reaction with 17 steps

1: 94 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 70 percent / DIBALH / diethyl ether / 0.67 h / -78 °C

3: tetrahydrofuran / 1 h / -78 - -20 °C

4: 1.) LiHMDSA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT, overnight

5: 1.) LiHMDSA, 2.) TBAF / 1.) THF, 0 deg C, 20 min, 2.) THF, RT, overnight

6: 84 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h

7: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, 15 min

8: t-BuOK / 2-methyl-propan-2-ol / 1 h / 0 °C

9: 100 percent / HF / acetonitrile / 0.17 h / 0 °C

10: 63 percent / DMAP / CH₂Cl₂ / 3 h / Ambient temperature

11: 74 percent / CrO₃, H₂SO₄ / acetone / 0.5 h / Ambient temperature

12: 86 percent / Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

13: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature

14: imidazole / dimethylformamide / 12 h / Ambient temperature

15: 94 percent / imidazole / dimethylformamide / Ambient temperature

16: 1.) LiHMDSA / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) -20 deg C, overnight

17: 72 percent / KF / methanol / 1.5 h

With 1H-imidazole; chromium(VI) oxide; dmap; potassium fluoride; LiHMDSA; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1016/0957-4166(96)00384-9

Reference yield:

4-(2-hydroxy-cyclohexyl)azetidin-2-one → (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one (184531-16-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 84 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, 15 min

3: t-BuOK / 2-methyl-propan-2-ol / 1 h / 0 °C

4: 100 percent / HF / acetonitrile / 0.17 h / 0 °C

5: 63 percent / DMAP / CH₂Cl₂ / 3 h / Ambient temperature

6: 74 percent / CrO₃, H₂SO₄ / acetone / 0.5 h / Ambient temperature

7: 86 percent / Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

8: H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / Ambient temperature

9: imidazole / dimethylformamide / 12 h / Ambient temperature

10: 94 percent / imidazole / dimethylformamide / Ambient temperature

11: 1.) LiHMDSA / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) -20 deg C, overnight

12: 72 percent / KF / methanol / 1.5 h

With 1H-imidazole; chromium(VI) oxide; dmap; potassium fluoride; LiHMDSA; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; hydrogen; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1016/0957-4166(96)00384-9

upstream raw materials:

(3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-[(S)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one

ephedrine

(2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one

cis-ethyl 2-hydroxy-cyclohexanoate

Downstream raw materials:

(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1S,2S,6S)-1-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-azetidin-2-one

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