(S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Base Information

• Chemical Name: (S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
• CAS No.: 872607-58-4
• Molecular Formula: C₁₉H₃₀N₂O₂Si
• Molecular Weight: 346.545

Synonyms:(S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property of (S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property:

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Technology Process of (S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

There total 1 articles about (S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 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: 68.0%

(4-bromo-2-butyn-1-yl)trimethylsilane (121823-55-0) + 2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide (170115-98-7) → (S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (872607-58-4)

Guidance literature:

2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide; With lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; for 0.333333h; cooling;

(4-bromo-2-butyn-1-yl)trimethylsilane; In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1021/ja056206n

Reference yield:

(S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (872607-58-4) → (Z)-(2R,3S)-3-{[1-((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-meth-(E)-ylidene]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile

Guidance literature:

Multi-step reaction with 9 steps

1.1: 72 percent / LiNH₂*BH₃ / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 98 percent / triethylamine / tetrahydrofuran / 1 h / 23 °C

3.1: 90 percent / sodim borohydride; Ni(OAc)2*4H₂O; ethylenediamine / ethanol / 3 h / 23 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 0 °C

5.1: acetic acid / methanol / 0.17 h / cooling

5.2: methanol; CH₂Cl₂ / 5 h / 0 °C

6.1: 2,2,2-trifluoro-ethanol / 14 h / 23 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 - 23 °C

8.1: sodium sulfate / benzene; CH₂Cl₂ / 2 h / 23 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.17 h / cooling

With sodium tetrahydroborate; lithium amidotrihydroborate; nickel diacetate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; ethylenediamine; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 2,2,2-trifluoroethanol; benzene;

DOI:10.1021/ja056206n

Reference yield:

(S)-2-Amino-6-trimethylsilanyl-hex-4-ynoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (872607-58-4) → (Z)-(2S,3S)-3-{[1-((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-meth-(E)-ylidene]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile

Guidance literature:

Multi-step reaction with 9 steps

1.1: 72 percent / LiNH₂*BH₃ / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 98 percent / triethylamine / tetrahydrofuran / 1 h / 23 °C

3.1: 90 percent / sodim borohydride; Ni(OAc)2*4H₂O; ethylenediamine / ethanol / 3 h / 23 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 0 °C

5.1: acetic acid / methanol / 0.17 h / cooling

5.2: methanol; CH₂Cl₂ / 5 h / 0 °C

6.1: 2,2,2-trifluoro-ethanol / 14 h / 23 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 - 23 °C

8.1: sodium sulfate / benzene; CH₂Cl₂ / 2 h / 23 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.17 h / cooling

With sodium tetrahydroborate; lithium amidotrihydroborate; nickel diacetate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; ethylenediamine; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 2,2,2-trifluoroethanol; benzene;

DOI:10.1021/ja056206n

upstream raw materials:

(4-bromo-2-butyn-1-yl)trimethylsilane

2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide

Downstream raw materials:

(Z)-(2R,3S)-3-{[((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-cyano-methyl]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile

(Z)-(2S,3S)-3-{[((1R,3S)-1-Benzyloxymethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinolin-3-yl)-cyano-methyl]-amino}-2-morpholin-4-yl-7-trimethylsilanyl-hept-5-enenitrile

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