methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

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Chemical Name:methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate
CAS No.:1361343-19-2
Molecular Formula:C₃₁H₄₂F₃N₅O₅Si
Molecular Weight:649.786
Hs Code.:

Synonyms:methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

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Chemical Property of methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

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Technology Process of methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

There total 8 articles about methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate 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: 71.0%

: N-α-trifluoroacetyl-L-lysine methyl ester

: 1361343-24-9
(2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoic acid

: 1361343-19-2
methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

Guidance literature:: (2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoic acid; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 4 ℃; for 0.0833333h; Inert atmosphere;

With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; In N,N-dimethyl-formamide; at 4 ℃; for 0.0833333h; Inert atmosphere;

N-α-trifluoroacetyl-L-lysine methyl ester; In N,N-dimethyl-formamide; at 4 - 20 ℃; for 2.25h; Inert atmosphere;
DOI:10.1021/ol300045c

Reference yield:

: 1012085-19-6
(2R,3R)-1-tert-butyl 5-methyl 2-amino-3-methylpentanedioate

: 1361343-19-2
methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydrogencarbonate / tetrahydrofuran; water / 12 h / 4 - 20 °C / pH 8.3 / Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran; water / 3.5 h / 4 - 20 °C / Inert atmosphere

3.1: N-ethylmorpholine; / tetrahydrofuran / -15 - 4 °C / Inert atmosphere

3.2: 4 - 20 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 11 h / 20 °C / Inert atmosphere

4.2: 3.5 h / 20 °C / Inert atmosphere

5.1: triethylsilane; trifluoroacetic acid / dichloromethane / 4.25 h / 4 - 20 °C / Inert atmosphere

6.1: triflic azide; triethylamine; zinc(II) chloride / methanol; dichloromethane; water / 5 h / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 4 °C / Inert atmosphere

7.2: 0.08 h / 4 °C / Inert atmosphere

7.3: 2.25 h / 4 - 20 °C / Inert atmosphere

With N-ethylmorpholine;; 1H-imidazole; triethylsilane; triflic azide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc(II) chloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol300045c

Reference yield:

: 1012085-22-1
(2R,3R)-1-tert-butyl 5-methyl 2-(2,2-dimethyl-1-phenylpropylideneamino)-3-methylpentanedioate

: 1361343-19-2
methyl (2S)-6-((2R,3R)-2-azido-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanamido)-2-(2,2,2-trifluoroacetamido)hexanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: hydrogenchloride / tetrahydrofuran; water / 0.5 h / 4 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / tetrahydrofuran; water / 12 h / 4 - 20 °C / pH 8.3 / Inert atmosphere

3.1: lithium hydroxide / tetrahydrofuran; water / 3.5 h / 4 - 20 °C / Inert atmosphere

4.1: N-ethylmorpholine; / tetrahydrofuran / -15 - 4 °C / Inert atmosphere

4.2: 4 - 20 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 11 h / 20 °C / Inert atmosphere

5.2: 3.5 h / 20 °C / Inert atmosphere

6.1: triethylsilane; trifluoroacetic acid / dichloromethane / 4.25 h / 4 - 20 °C / Inert atmosphere

7.1: triflic azide; triethylamine; zinc(II) chloride / methanol; dichloromethane; water / 5 h / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / 4 °C / Inert atmosphere

8.2: 0.08 h / 4 °C / Inert atmosphere

8.3: 2.25 h / 4 - 20 °C / Inert atmosphere

With N-ethylmorpholine;; 1H-imidazole; hydrogenchloride; triethylsilane; triflic azide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc(II) chloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol300045c