methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

Base Information

Chemical Name:methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide
CAS No.:1088409-91-9
Molecular Formula:C₂₇H₃₈N₄O₅S₃
Molecular Weight:594.821
Hs Code.:

Synonyms:methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

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Chemical Property of methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

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Technology Process of methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

There total 15 articles about methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-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:

: methyl (7S)-6-N-((2′S,4′R)-1′-N-(tert-butoxycarbonyl)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

: 1088409-91-9
methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1038/ja.2017.114

Reference yield:

: C₃₆H₇₄N₂O₈SSi₄

: 1088409-91-9
methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

Guidance literature:: Multi-step reaction with 7 steps

1: acetic acid / methanol / 2.33 h / 20 °C

2: triethylamine / dichloromethane / 0 - 20 °C

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

4: hydrogenchloride / methanol; water / 0.08 h / 20 °C

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

6: 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

7: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium methylate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1038/ja.2017.114

Reference yield:

: 1088411-18-0
methyl 6-N-((2S,4R)-1-(tert-butoxycarbonyl)-4-(cyclopropylmethyl)piperidine-2-carbonyl)-7-O-methanesulphonyl-1-thio-2,3,4-tris-O-trimethylsilyl-α-lincosamide

: 1088409-91-9
methyl (7S)-6-N-((2′S,4′R)-4′-(cyclopropylmethyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)-α-thiolincosaminide

Guidance literature:: Multi-step reaction with 5 steps

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

2: hydrogenchloride / methanol; water / 0.08 h / 20 °C

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

4: 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

5: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium methylate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1038/ja.2017.114