methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate

Base Information

• Chemical Name: methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate
• CAS No.: 1607826-46-9
• Molecular Formula: C₂₃H₂₁NO₉S
• Molecular Weight: 487.487

Synonyms:methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate

Chemical Property of methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate

Chemical Property:

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Technology Process of methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate

There total 4 articles about methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate 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: 92.0%

methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2,3-dihydroxypropanoate (1607826-45-8) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate (1607826-46-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja502744a

Reference yield:

benzyl bromide (100-39-0) → methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate (1607826-46-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 4 h / 23 °C / Reflux; Inert atmosphere

2: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 72 h / 0 °C / Inert atmosphere

3: triethylamine / dichloromethane / 6 h / 0 °C / Inert atmosphere

With methanesulfonamide; AD-mix β; potassium carbonate; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja502744a

Reference yield:

methyl 4-hydroxycinnamate (3943-97-3) → methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-3-hydroxy-2-(((2-nitrophenyl)sulfonyl)oxy)propanoate (1607826-46-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 4 h / 23 °C / Reflux; Inert atmosphere

2: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 72 h / 0 °C / Inert atmosphere

3: triethylamine / dichloromethane / 6 h / 0 °C / Inert atmosphere

With methanesulfonamide; AD-mix β; potassium carbonate; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja502744a

upstream raw materials:

methyl (2S,3R)-3-(4-(benzyloxy)phenyl)-2,3-dihydroxypropanoate

2-Nitrobenzenesulfonyl chloride

benzyl bromide

methyl 4-hydroxycinnamate

Downstream raw materials:

methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

methyl (2R,3R)-2-azido-3-(4-(benzyloxy)phenyl)-3-methoxypropanoate

methyl (2R,3R)-2-amino-3-(4-hydroxyphenyl)-3-methoxypropanoate

methyl (2R,3R)-2-(((allyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)-3-methoxypropanoate

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