methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide

Base Information

• Chemical Name: methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide
• CAS No.: 1089133-87-8
• Molecular Formula: C₂₁H₃₁F₃N₂O₅S₂
• Molecular Weight: 512.615
• Mol file: 1089133-87-8.mol

Synonyms:methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide

Chemical Property of methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide

There total 8 articles about methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-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: 94.0%

→ methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide (1089133-87-8)

Guidance literature:

Reference yield: 80.0%

2,2,2-trifluoro-N-((1S,2S)-2-mercapto-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)acetamide (1089133-84-5) + 2-(4-bromophenyl)-N,N-dimethylethan-1-amine (15221-61-1) → methyl (7S)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide (1089133-87-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 17h; Reflux;

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)-7-deoxy-7-(4-(2-dimethylaminoethyl)phenyl)thio-6-N-(2,2,2-trifluoroacetyl)-α-thiolincosaminide (1089133-87-8)

Guidance literature:

Multi-step reaction with 4 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

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; methanol; 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

2,2,2-trifluoro-N-((1S,2S)-2-mercapto-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)acetamide

2-(4-bromophenyl)-N,N-dimethylethan-1-amine

Downstream raw materials:

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

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

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