(8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

Base Information

• Chemical Name: (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid
• CAS No.: 685869-22-1
• Molecular Formula: C₃₉H₄₉FN₄O₁₂Si
• Molecular Weight: 812.922

Synonyms:(8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

Chemical Property of (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

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Technology Process of (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

There total 14 articles about (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid 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: 79.0%

{11-[(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-8-hydroxymethyl-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]eicosa-1(18),3(20),4,6,15(19),16-hexaen-14-yl}-carbamic acid tert-butyl ester (685869-40-3) → (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid (685869-22-1)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at -10 - 0 ℃;

DOI:10.1021/ja039795a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid (685869-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.1 mg / NaHCO₃ / dimethylformamide / 13 h / 25 °C

2: 79 percent / CrO₃; aq. H₂SO₄ / acetone / -10 - 0 °C

With chromium(VI) oxide; sulfuric acid; sodium hydrogencarbonate; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja039795a

Reference yield:

ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate (685869-24-3) → (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-[(R)-(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid (685869-22-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

2: Et₃N / dioxane / 18 h / 25 °C

3: aq. LiOH / 2-methyl-propan-2-ol / 18 h / 25 °C

4: 79 percent / NaHCO₃; HATU / tetrahydrofuran / 48 h / 0 °C

5: 81 percent / CrO₃; aq. H₂SO₄ / acetone / 2 h / 0 °C

6: 96 percent / Bu₄NF / tetrahydrofuran / 11.5 h / 25 °C

7: 92 percent / benzotriazol-1-yloxytrispyrrolidinophosphonium*PF₆^(1-); NaHCO₃ / CH₂Cl₂; dimethylformamide / 5 h / 25 °C

8: 96 percent / acetonitrile / 1.5 h / 42 °C

9: B-bromocatecholborane / CH₂Cl₂ / 2.5 h / 0 °C

10: 3.1 mg / NaHCO₃ / dimethylformamide / 13 h / 25 °C

11: 79 percent / CrO₃; aq. H₂SO₄ / acetone / -10 - 0 °C

With 2,6-dimethylpyridine; chromium(VI) oxide; lithium hydroxide; sulfuric acid; bromocatecholborane; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja039795a

upstream raw materials:

{11-[(tert-butyl-dimethyl-silanyloxy)-(4-fluoro-3-nitro-phenyl)-methyl]-8-hydroxymethyl-5,18-dimethoxy-4-methyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]eicosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaen-14-yl}-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-hydroxypropionate

ethyl (2R,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate

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