(2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate

Base Information

• Chemical Name: (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate
• CAS No.: 218914-99-9
• Molecular Formula: C₂₄H₂₃NO₉S
• Molecular Weight: 501.514

Synonyms:(2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate

Chemical Property of (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate

Chemical Property:

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Technology Process of (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate

There total 6 articles about (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)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%

4-Nitrobenzenesulfonyl chloride (98-74-8) + (2S,3R)-ethyl 3-(4-(benzyloxy)phenyl)-2,3-dihydroxypropanoate → (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate (218914-99-9)

Guidance literature:

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

DOI:10.1039/c3ra44631j

Reference yield: 68.0%

4-Nitrobenzenesulfonyl chloride (98-74-8) + 3-(4-benzyloxy-phenyl)-2,3-dihydroxy-propionic acid ethyl ester → (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate (218914-99-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

(E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate (104315-07-3) → (2S,3R)-ethyl-(4-(benzyloxy)phenyl)-3-hydroxy-2-(4-nitrophenylsulfonyloxy)propanoate (218914-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 16 h / 0 - 20 °C

2: triethylamine / dichloromethane / 6 h / 0 °C

With methanesulfonamide; AD-mix β; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: |Sharpless Dihydroxylation;

DOI:10.1039/c3ra44631j

upstream raw materials:

4-Nitrobenzenesulfonyl chloride

(E)-ethyl 3-(4-(benzyloxy)phenyl)acrylate

p-benzyloxybenzaldehyde

4-hydroxy-benzaldehyde

Downstream raw materials:

(4S,5R)-5-(4-Benzyloxy-phenyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

(2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid

(2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionic acid ethyl ester

(S)-2-{(2R,3R)-3-(4-Benzyloxy-phenyl)-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-hydroxy-propionylamino}-N-[bis-(4-methoxy-phenyl)-methyl]-succinamic acid methyl ester

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