7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

Base Information

Chemical Name:7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin
CAS No.:941585-41-7
Molecular Formula:C₃₃H₄₇N₃O₇S₂
Molecular Weight:661.884
Hs Code.:

Synonyms:7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

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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 7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

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Technology Process of 7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

There total 9 articles about 7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin 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: 80.4%

: 129013-83-8
3-(4-bromophenyl)pyridine

: 941585-39-3
7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-mercaptolincomycin

: 941585-41-7
7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 5h; Reflux;
DOI:10.1038/ja.2017.54

Reference yield:

: 941585-36-0
7(S)-7-acetylthio-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-2,3,4-tris-O-(trimethylsilyl)lincomycin

: 941585-41-7
7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogenchloride / methanol; water / 1 h / 20 °C

2: sodium methylate; methanol / 1.5 h / 20 °C

3: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / Reflux

With hydrogenchloride; methanol; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium methylate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; methanol; water;
DOI:10.1038/ja.2017.54

Reference yield:

: 540501-47-1
(2S,4R)-N-tert-butyloxycarbonyl-4-propylproline

: 941585-41-7
7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{4-(pyridin-3-yl)phenylthio}lincomycin

Guidance literature:: Multi-step reaction with 8 steps

1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 15 h / 20 °C

2: 1,1,1,3,3,3-hexamethyl-disilazane; pyridine / 0.5 h / 20 °C

3: acetic acid / methanol / 11 h / 20 °C

4: methanesulfonyl chloride; triethylamine / chloroform / 0.5 h / 20 °C

5: potassium carbonate / N,N-dimethyl-formamide / 10 h / 60 °C

6: hydrogenchloride / methanol; water / 1 h / 20 °C

7: sodium methylate; methanol / 1.5 h / 20 °C

8: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / Reflux

With pyridine; hydrogenchloride; methanol; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium methylate; potassium carbonate; benzotriazol-1-ol; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; methanol; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1038/ja.2017.54