(4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone

Base Information

• Chemical Name: (4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone
• CAS No.: 134848-81-0
• Molecular Formula: C₁₆H₂₇NO₅
• Molecular Weight: 313.394

Synonyms:(4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone

Chemical Property of (4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone

There total 1 articles about (4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone 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: 95.0%

3-[2-((4S,5R)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-[1,3]dioxolan-2-yl]-propionic acid (134848-98-9) → (4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone (134848-81-0)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jm00113a005

Reference yield:

(4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone (134848-81-0) → (3S,11R,12R,13S)-3-Amino-13-cyclohexylmethyl-11,12-dihydroxy-1,7-diaza-cyclotridecane-2,6-dione

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: LiN₃ / dimethylformamide / Ambient temperature

3: 992 mg / Ba(OH)2 / dioxane; H₂O / Heating

4: 1 N aq. HCl / 60 - 65 °C

5: NaHCO₃ / tetrahydrofuran; H₂O / 4 °C

6: 57 percent / NaBH₄ / methanol / 0.25 h / 0 °C

7: TFA / CH₂Cl₂ / Ambient temperature

8: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

9: 52 percent / H₂, AcOH / 10percent Pd/C / methanol; tetrahydrofuran / 2068.6 Torr

10: 45 percent / diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

11: TFA / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; lithium azide; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a005

Reference yield:

(4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone (134848-81-0) → (3S,11S,12R,13S)-3-Amino-13-cyclohexylmethyl-11,12-dihydroxy-1,7-diaza-cyclotridecane-2,6-dione

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: LiN₃ / dimethylformamide / Ambient temperature

3: 992 mg / Ba(OH)2 / dioxane; H₂O / Heating

4: 1 N aq. HCl / 60 - 65 °C

5: NaHCO₃ / tetrahydrofuran; H₂O / 4 °C

6: 44 percent / NaBH₄ / methanol / 0.25 h / 0 °C

7: TFA / CH₂Cl₂ / Ambient temperature

8: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

9: 56 percent / H₂, AcOH / 10percent Pd/C / methanol; tetrahydrofuran / 2068.6 Torr

10: 34 percent / diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

11: TFA / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; lithium azide; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a005

upstream raw materials:

3-[2-((4S,5R)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-[1,3]dioxolan-2-yl]-propionic acid

Downstream raw materials:

Methanesulfonic acid 3-[2-((4S,5R)-4-cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-[1,3]dioxolan-2-yl]-propyl ester

(1R,2S)-2-Amino-1-[2-(3-azido-propyl)-[1,3]dioxolan-2-yl]-3-cyclohexyl-propan-1-ol

(4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-azidopropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone

(2S,3R)-7-azido-1-cyclohexyl-2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-4-oxoheptane

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