methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

Base Information

Chemical Name:methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate
CAS No.:1314795-29-3
Molecular Formula:C₂₉H₄₇NO₅SSi
Molecular Weight:549.847
Hs Code.:

Synonyms:methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

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Chemical Property of methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

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Technology Process of methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

There total 13 articles about methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate 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%

: 1314795-28-2
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 1314795-29-3
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

Guidance literature:: methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate; With triethylamine; In dichloromethane; for 0.166667h;

triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jm401420j

Reference yield:

: 1263101-14-9
5-(3,3-dimethylbut-1-ynyl)-3-((1R,2S,4R)-2-hydroxy-4-methyl-N-((1r,4R)-4-(tetrahydrofuran-3-yloxy)cyclohexyl)cyclohexanecarboxamido)thiophene-2-carboxylic acid

: 1314795-29-3
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.25 h / 20 °C

1.2: 3 h

2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0.25 h / 20 °C

2.2: 24 h / 40 °C

3.1: triethylamine / dichloromethane / 0.17 h

3.2: 0.5 h / -78 °C

With potassium tert-butylate; sodium hydride; triethylamine; In 1-methyl-pyrrolidin-2-one; dichloromethane; dimethyl sulfoxide; mineral oil;
DOI:10.1021/jm401420j

Reference yield:

: 1485470-44-7
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1s,4s)-4-(tetrahydrofuran-3-yloxy)cyclohexylamino)thiophene-2-carboxylate

: 1314795-29-3
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-(((S)-tetrahydrofuran-3-yloxy)methyl)-4-(triethylsilyloxy)cyclohexylamino)thiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1,2-dichloro-ethane / 70 °C

2.1: lithium hydroxide / tetrahydrofuran; water / 20 °C

3.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.25 h / 20 °C

3.2: 3 h

4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0.25 h / 20 °C

4.2: 24 h / 40 °C

5.1: triethylamine / dichloromethane / 0.17 h

5.2: 0.5 h / -78 °C

With potassium tert-butylate; sodium hydride; triethylamine; lithium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; mineral oil;
DOI:10.1021/jm401420j