2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

Base Information

• Chemical Name: 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal
• CAS No.: 122777-42-8
• Molecular Formula: C₂₁H₂₄O₁₁
• Molecular Weight: 452.415

Synonyms:2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

Chemical Property of 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

There total 10 articles about 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal 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: 66.0%

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal (127213-09-6) → 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal (122777-42-8)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 5 ℃; for 14h;

DOI:10.1021/jo00009a009

Reference yield:

methyl 2,3-di-O-benzyl-α-D-altropyranoside (33164-03-3) → 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal (122777-42-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / diethyl azodicarboxylate, triphenylphosphine, CH₃I / tetrahydrofuran / 19 h / Ambient temperature

2: DBU / toluene / 23 h / 80 °C

3: Amberlite IR 120 B resin / tetrahydrofuran; H₂O / 22 h / Ambient temperature

4: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

5: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

6: 96 percent / pyridine / Ambient temperature

7: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

8: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; methyl iodide; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/jo00009a009

Reference yield:

methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside (118068-39-6) → 2-acetoxy-4-formylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal (122777-42-8)

Guidance literature:

Multi-step reaction with 7 steps

1: DBU / toluene / 23 h / 80 °C

2: Amberlite IR 120 B resin / tetrahydrofuran; H₂O / 22 h / Ambient temperature

3: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

4: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

5: 96 percent / pyridine / Ambient temperature

6: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

7: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/jo00009a009

upstream raw materials:

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside

methyl 2,3-di-O-benzyl-α-D-altropyranoside

(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

Downstream raw materials:

2-acetoxy-4-<(E)-2-(ethoxycarbonyl)-1-propen-1-yl>phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

hygromycin A

2-acetoxy-4-<(E)-2-carboxy-1-propen-1-yl>phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

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