(8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione

Base Information

• Chemical Name: (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione
• CAS No.: 173775-57-0
• Molecular Formula: C₂₅H₂₄N₄O₇
• Molecular Weight: 492.488

Synonyms:(8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione

Chemical Property of (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione

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Technology Process of (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione

There total 20 articles about (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione 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: 73.0%

[(8R,11S,14R)-8-Hydroxymethyl-11-(3-isopropoxy-phenyl)-19-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaen-14-yl]-carbamic acid tert-butyl ester (173775-56-9) → (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-10,13-dione (173775-57-0)

Guidance literature:

With hydrogenchloride; boron trichloride; In acetonitrile;

DOI:10.1016/0040-4039(95)01876-J

Reference yield:

C16H22O4 → (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-10,13-dione (173775-57-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / Et₃N / tetrahydrofuran / 0.25 h / -78 °C

2: 1.) KHDMS, 2.) trisyl azide / 1.) THF_. -78 deh C, 30 min, 2.) THF, -78 deg C, 4 min

3: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

4: 92 percent / LiOH / tetrahydrofuran; H₂O

5: 92 percent / EDC, HOBt / CH₂Cl₂ / 0.5 h / 0 °C

6: 85 percent / NaBH₄, Pd(PPh₃)4 / tetrahydrofuran / 1 h / Ambient temperature

7: 2,6-lutidine / 0.33 h / Ambient temperature

8: 2,6-lutidine, NH₄Cl, HCl / H₂O / 0.25 h / Ambient temperature

9: 95 percent / EDC, HOBt / CH₂Cl₂ / 0.67 h / Ambient temperature

10: 84 percent / CsF / dimethylformamide / 15 h / Ambient temperature

11: 1.) BCl₃, 2.) HCl / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) MeCN, rt, 1 h

With 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; boron trichloride; potassium hexamethylsilazane; ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo961412m

Reference yield:

(S)-4-Benzyl-3-[2-(3-isopropoxy-phenyl)-acetyl]-oxazolidin-2-one (185112-27-0) → (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-10,13-dione (173775-57-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) KHDMS, 2.) trisyl azide / 1.) THF_. -78 deh C, 30 min, 2.) THF, -78 deg C, 4 min

2: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

3: 92 percent / LiOH / tetrahydrofuran; H₂O

4: 92 percent / EDC, HOBt / CH₂Cl₂ / 0.5 h / 0 °C

5: 85 percent / NaBH₄, Pd(PPh₃)4 / tetrahydrofuran / 1 h / Ambient temperature

6: 2,6-lutidine / 0.33 h / Ambient temperature

7: 2,6-lutidine, NH₄Cl, HCl / H₂O / 0.25 h / Ambient temperature

8: 95 percent / EDC, HOBt / CH₂Cl₂ / 0.67 h / Ambient temperature

9: 84 percent / CsF / dimethylformamide / 15 h / Ambient temperature

10: 1.) BCl₃, 2.) HCl / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) MeCN, rt, 1 h

With 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; boron trichloride; potassium hexamethylsilazane; ammonium chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo961412m

upstream raw materials:

[(8R,11S,14R)-8-Hydroxymethyl-11-(3-isopropoxy-phenyl)-19-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaen-14-yl]-carbamic acid tert-butyl ester

D-<2-<(tert-butyldimethylsilyl)oxy>-1-<3-(allyloxy)phenyl>ethyl>amine

(2R,4R)-3-<2-azido-2-<3-(allyloxy)phenyl>-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine

Downstream raw materials:

2-(3-Fluoro-4-nitro-phenyl)-N-[(8R,11S,14R)-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaen-14-yl]-acetamide

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