1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate

Base Information

• Chemical Name: 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate
• CAS No.: 1359014-81-5
• Molecular Formula: C₃₇H₃₆N₂O₇S₂
• Molecular Weight: 684.834

Synonyms:1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate

Chemical Property of 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate

Chemical Property:

Purity/Quality:

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Technology Process of 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate

There total 4 articles about 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N₂-(benzyloxycarbonyl)-N₆-(9H-fluoren-9-yl) lanthionate 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: 70.0%

C31H32N2O8S + thiophenol (108-98-5) → 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N2-(benzyloxycarbonyl)-N6-(9H-fluoren-9-yl) lanthionate (1359014-81-5)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol203399x

Reference yield:

(2S,3S)-methyl 3-(((R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)thio)-2-(((benzyloxy)carbonyl)amino)butanoate (1359015-32-9) → 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N2-(benzyloxycarbonyl)-N6-(9H-fluoren-9-yl) lanthionate (1359014-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / ethyl acetate / 20 h / 20 °C / Inert atmosphere

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; ethyl acetate;

DOI:10.1021/ol203399x

Reference yield:

(R)-β-bromo-N-(fluoren-9-ylmethoxycarbonyl)alanine tert-butyl ester (634182-11-9) → 1-O-methyl-3-methyl-7-S-phenyl-(2S,3S,6S)-N2-(benzyloxycarbonyl)-N6-(9H-fluoren-9-yl) lanthionate (1359014-81-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetra(n-butyl)ammonium hydrogensulfate; caesium carbonate / ethyl acetate / 20 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / ethyl acetate / 20 h / 20 °C / Inert atmosphere

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; tetra(n-butyl)ammonium hydrogensulfate; caesium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; ethyl acetate;

DOI:10.1021/ol203399x

upstream raw materials:

thiophenol

(2S,3S)-methyl 3-(((R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)thio)-2-(((benzyloxy)carbonyl)amino)butanoate

(2S,3S)-N-benzyloxycarbonyl-3-methylcysteine methyl ester

(R)-β-bromo-N-(fluoren-9-ylmethoxycarbonyl)alanine tert-butyl ester

Downstream raw materials:

(5S,6S,Z)-methyl 13-(9H-fluoren-9-yl)-6-methyl-3,11-dioxo-1-phenyl-2,12-dioxa-7-thia-4,10-diazatridec-8-ene-5-carboxylate

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