(1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

Base Information

Chemical Name:(1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide
CAS No.:328123-50-8
Molecular Formula:C₂₈H₃₆NO₂PS
Molecular Weight:481.639
Hs Code.:

Synonyms:(1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

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Chemical Property of (1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

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Technology Process of (1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

There total 6 articles about (1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-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:

: 125637-45-8
(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid methylester

: 328123-50-8
(1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C

2.1: triethylamine; Ph₂P(CH₂)4PPh₂ / Pd(OAc)2 / benzene / 24 h / 90 °C

3.1: 1.20 g / S₈ / toluene / 20 °C

4.1: 98 percent / LiI / pyridine / 24 h / Heating

5.1: EDC; HOBT; triethylamine / various solvent(s) / 20 °C

5.2: 226 mg / triethylamine / dimethylformamide

With sulfur; n-butyllithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; diisopropylamine; 1,4-di(diphenylphosphino)-butane; lithium iodide; palladium diacetate; In tetrahydrofuran; pyridine; hexane; toluene; benzene;
DOI:10.1021/ol006747b

Reference yield:

: 464-78-8,6994-94-1,64234-14-6,40724-67-2
(1S)-(+)-ketopinic acid

: 328123-50-8
(1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / SOCl₂ / 20 °C

2.1: 93 percent / n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C

3.1: triethylamine; Ph₂P(CH₂)4PPh₂ / Pd(OAc)2 / benzene / 24 h / 90 °C

4.1: 1.20 g / S₈ / toluene / 20 °C

5.1: 98 percent / LiI / pyridine / 24 h / Heating

6.1: EDC; HOBT; triethylamine / various solvent(s) / 20 °C

6.2: 226 mg / triethylamine / dimethylformamide

With sulfur; n-butyllithium; thionyl chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; diisopropylamine; 1,4-di(diphenylphosphino)-butane; lithium iodide; palladium diacetate; In tetrahydrofuran; pyridine; hexane; toluene; benzene;
DOI:10.1021/ol006747b

Reference yield:

: 328123-48-4
methyl (1S,4R)-7,7-dimethyl-2-(trifluoromethylsulfonyloxy)bicyclo[2.2.1]hept-2-ene-1-carboxylate

: 328123-50-8
(1R,4R)-2-(Diphenyl-phosphinothioyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; Ph₂P(CH₂)4PPh₂ / Pd(OAc)2 / benzene / 24 h / 90 °C

2.1: 1.20 g / S₈ / toluene / 20 °C

3.1: 98 percent / LiI / pyridine / 24 h / Heating

4.1: EDC; HOBT; triethylamine / various solvent(s) / 20 °C

4.2: 226 mg / triethylamine / dimethylformamide

With sulfur; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 1,4-di(diphenylphosphino)-butane; lithium iodide; palladium diacetate; In pyridine; toluene; benzene;
DOI:10.1021/ol006747b