(2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester

Base Information

• Chemical Name: (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester
• CAS No.: 224044-68-2
• Molecular Formula: C₂₅H₂₇NO₁₅
• Molecular Weight: 581.487
• DSSTox Substance ID: DTXSID60472966
• Nikkaji Number: J1.142.784G
• Wikidata: Q82302155
• Mol file: 224044-68-2.mol

Synonyms:224044-68-2;(2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester;methyl (E)-4-[2-nitro-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]-4-oxobut-2-enoate;FT-0673007;DTXSID60472966;(2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-|A-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester;methyl (E)-4-[2-nitro-3-[(2S, 3R, 4S, 5R, 6R)-3, 4, 5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]-4-oxobut-2-enoate

Chemical Property of (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester

Chemical Property:

• Solubility.: Acetone, Chloroform, Dichloromethane
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 15
• Exact Mass: 581.13806915
• Heavy Atom Count: 41
• Complexity: 1050

Purity/Quality:

97% ^*data from raw suppliers

(2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=CC(=C2[N+](=O)[O-])C(=O)C=CC(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC(=C2[N+](=O)[O-])C(=O)/C=C/C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester is used in the preparation of human UV filters.

Technology Process of (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester

There total 1 articles about (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester 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:

(E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoic acid (93367-77-2,224044-66-0) → methyl (E)-4-oxo-4-<2-nitro-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate (224044-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / DCC / CH₂Cl₂ / Ambient temperature

2: 61 percent / Hg(CN)2, K₂CO₃ / acetonitrile / 4 h / Ambient temperature

With mercury(II) cyanide; potassium carbonate; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;

DOI:10.1021/jo982321n

Reference yield: 63.0%

methyl (E)-4-oxo-4-<2-nitro-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate (224044-68-2) → methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate (224044-69-3)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; ethyl acetate; for 12h; under 760 Torr;

DOI:10.1021/jo982321n

Reference yield:

methyl (E)-4-oxo-4-<2-nitro-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate (224044-68-2) → 2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid (156913-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / H₂ / PtO₂ / ethanol; ethyl acetate / 12 h / 760 Torr

2: EtONa / ethanol / 2 h / Ambient temperature

3: NaOH / H₂O / 4 h / Ambient temperature

With sodium hydroxide; hydrogen; sodium ethanolate; platinum(IV) oxide; In ethanol; water; ethyl acetate;

DOI:10.1021/jo982321n

upstream raw materials:

(E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoic acid

Downstream raw materials:

methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate

2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid

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