(6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid

Base Information

• Chemical Name: (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid
• CAS No.: 1345116-64-4
• Molecular Formula: C₄₁H₅₇N₃O₈Si
• Molecular Weight: 748.004
• Mol file: 1345116-64-4.mol

Synonyms:(6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid

Chemical Property of (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid

There total 12 articles about (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic 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: 78.0%

(6R,8S,11S,14S)-ethyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate (1345116-62-2) → (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid (1345116-64-4)

Guidance literature:

(6R,8S,11S,14S)-ethyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate; With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 2h; Inert atmosphere;

With potassium hydrogensulfate; In tetrahydrofuran; water; Inert atmosphere; Saturated solution;

DOI:10.1016/j.tetasy.2011.08.026

Reference yield:

tert-butyl (2S,4R)-5-(tert-butyldiphenylsilyloxy)-1-hydroxy-4-methylpentan-2-ylcarbamate (1345116-48-4) → (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid (1345116-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 3 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

2.2: 48 h / 20 °C / Inert atmosphere

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere; Saturated solution

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetasy.2011.08.026

Reference yield:

(S)-tert-butyl 4-((R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate (1345116-45-1) → (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid (1345116-64-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: methanol; toluene-4-sulfonic acid / 2 h / 0 °C / Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 3 h / 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

3.2: 48 h / 20 °C / Inert atmosphere

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

4.2: 24 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

5.2: Inert atmosphere; Saturated solution

With methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetasy.2011.08.026

upstream raw materials:

C₁₁H₁₉NO₄

tert-butyl [(1S,3R)-4-hydroxy-1-(hydroxymethyl)-3-methylbutyl]carbamate

(S)-tert-butyl 4-((R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

tert-butyl (2S,4R)-5-(tert-butyldiphenylsilyloxy)-1-hydroxy-4-methylpentan-2-ylcarbamate

Downstream raw materials:

(6R,8S,11R,14S)-methyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate

(6S,9R,12S)-methyl 6-((R)-3-(benzoyloxy)-2-methylpropyl)-12-((R)-methoxy(phenyl)methyl)-2,2,5,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate