methyl (7S)-6-N-((2′S,4′R)-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)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide
• CAS No.: 1089128-57-3
• Molecular Formula: C₂₉H₄₇N₃O₅S₂
• Molecular Weight: 581.841
• Mol file: 1089128-57-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about methyl (7S)-6-N-((2′S,4′R)-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: 99.0%

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 (1089132-37-5) → methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide (1089128-57-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3.5h;

DOI:10.1038/ja.2017.114

Reference yield:

methyl 7-acetylthio-7-deoxy-7-epi-1-thio-6-N-trifluoroacetyl-α-lincosamide (1089133-81-2) → methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide (1089128-57-3)

Guidance literature:

Multi-step reaction with 5 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

5: trifluoroacetic acid / dichloromethane / 3.5 h / 0 °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; trifluoroacetic acid; potassium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1038/ja.2017.114

Reference yield:

methyl 7-O-methaneslufonyl-6-N-(2,2,2-trifluoroacetyl)-2,3,4-tris-O-(trimethylsilyl)-α-thiolincosaminide (1089133-75-4) → methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-α-thiolincosaminide (1089128-57-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / N,N-dimethyl-formamide / 1.5 h / 80 °C

1.2: 3 h / 20 °C

2.1: hydrogenchloride / methanol; water / 0.17 h / 20 °C

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

4.1: 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

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

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

7.1: trifluoroacetic acid / dichloromethane / 3.5 h / 0 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-benzyl-N,N,N-triethylammonium chloride; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid; potassium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1038/ja.2017.114

upstream raw materials:

methyl 7-O-methaneslufonyl-6-N-(2,2,2-trifluoroacetyl)-2,3,4-tris-O-(trimethylsilyl)-α-thiolincosaminide

methyl 7-acetylthio-7-deoxy-7-epi-1-thio-6-N-trifluoroacetyl-α-lincosamide

4-(cyclopropylmethyl)pyridine

4-(cyclopropylmethyl)picolinonitrile

Downstream raw materials:

methyl 7-deoxy-7-(4-(2-(dimethylamino)ethyl)phenylthio)-7-epi-6-N-((2S,4R)-(4-cyclopropylmethyl-1-ethyl)piperidine-2-carbonyl)-1-thio-α-lincosamide

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