methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

Base Information

Chemical Name:methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate
CAS No.:1263101-57-0
Molecular Formula:C₂₆H₄₂INO₄SSi
Molecular Weight:619.68
Hs Code.:

Synonyms:methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

Chemical Property:

Purity/Quality:: 99% ^*data from raw suppliers

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Technology Process of methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

There total 9 articles about methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-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: 45.0%

: 1485469-39-3
methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)thiophene-2-carboxylate

: 1263101-57-0
methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

Guidance literature:: methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)thiophene-2-carboxylate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -75 - -60 ℃; for 2h;

With iodine; In tetrahydrofuran; hexane; at -78 ℃; for 3h;
DOI:10.1021/jm401420j

Reference yield:

: 934-67-8,4331-54-8,13064-83-0
trans-4-methylcyclohexanecarboxylic acid

: 1263101-57-0
methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dichloromethane; N,N-dimethyl-formamide / 3 h / 0 - 20 °C

2.1: pyridine / toluene / 16 h / Reflux

3.1: hydrogenchloride / tetrahydrofuran / 12 h / 40 °C

4.1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / -25 °C

5.1: 1H-imidazole / dichloromethane / 10 h / 0 - 9 °C / Inert atmosphere

6.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C

6.2: 3 h / -78 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm401420j

Reference yield:

: 55930-23-9
trans-4-methylcyclohexanecarbonyl chloride

: 1263101-57-0
methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / toluene / 16 h / Reflux

2.1: hydrogenchloride / tetrahydrofuran / 12 h / 40 °C

3.1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / -25 °C

4.1: 1H-imidazole / dichloromethane / 10 h / 0 - 9 °C / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C

5.2: 3 h / -78 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/jm401420j