methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

Base Information

Chemical Name:methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide
CAS No.:1089132-37-5
Molecular Formula:C₃₄H₅₅N₃O₇S₂
Molecular Weight:681.959
Hs Code.:

methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

Synonyms:methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

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Chemical Property of methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

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Technology Process of methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

There total 19 articles about methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide 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: 73.0%

: 1278587-60-2
methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

: (2S,4R)-N-(tert-butoxycarbonyl)-4-(cyclopropylmethyl)piperidine-2-carboxylic acid

: 1089132-37-5
methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 5.5h;
DOI:10.1038/ja.2017.114

Reference yield: 73.0%

: 1089132-37-5
methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

Guidance literature:

Reference yield:

: 1089133-81-2
methyl 7-acetylthio-7-deoxy-7-epi-1-thio-6-N-trifluoroacetyl-α-lincosamide

: 1089132-37-5
methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide

Guidance literature:: Multi-step reaction with 4 steps

1: sodium methylate / methanol / 0.25 h / 20 °C

2: 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 / 17 h / Reflux

3: N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide / dichloromethane; water / 4 h / 20 °C

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 5.5 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-benzyl-N,N,N-triethylammonium chloride; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; potassium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1038/ja.2017.114