7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin

Base Information

• Chemical Name: 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin
• CAS No.: 941586-83-0
• Molecular Formula: C₂₅H₃₅N₅O₇S₃
• Molecular Weight: 613.78

Synonyms:7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin

Chemical Property of 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin

Chemical Property:

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Technology Process of 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin

There total 6 articles about 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}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: 31.0%

→ 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin (941586-83-0)

Guidance literature:

Reference yield:

7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin (941585-43-9) → 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin (941586-83-0)

Guidance literature:

With hydrogenchloride; In methanol; water; ethyl acetate; at 20 ℃; for 2.5h;

DOI:10.1038/ja.2017.54

Reference yield:

1′-N-(tert-butoxycarbonyl)-1′-demethyl-2,3,4-tris-O-(trimethylsilyl)lincomycin (941585-28-0) → 7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin (941586-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 7 h / 20 °C

2: hydrogenchloride / methanol; water / 2.5 h / 20 °C

3: hydrogenchloride / methanol; water; ethyl acetate / 2.5 h / 20 °C

With hydrogenchloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; ethyl acetate;

DOI:10.1038/ja.2017.54

upstream raw materials:

benzyl (2S,4R)-4-allyl-1N-tert-butoxycarbonylpyrrolidine-2-carboxylate

1′-N-(tert-butoxycarbonyl)-1′-demethyllincomycin

1′-N-(tert-butoxycarbonyl)-1′-demethyl-2,3,4-tris-O-(trimethylsilyl)lincomycin

7(S)-1′-N-(tert-butoxycarbonyl)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-ylthio}lincomycin

Downstream raw materials:

7(S)-1′-demethyl-7-deoxy-7-{5-(2-nitrophenyl)-1,3,4-thiadiazol-2-yl}thio-1′-N-i-propyllincomycin

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