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

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Chemical Name: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
CAS No.:122777-35-9
Molecular Formula:C₂₄H₂₈O₁₂
Molecular Weight:508.479
Hs Code.:

Synonyms:

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Chemical Property of 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

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Technology Process of 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

There total 14 articles about 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 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:

: 33164-03-3
methyl 2,3-di-O-benzyl-α-D-altropyranoside

: 122777-35-9,127304-68-1
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

Guidance literature:: Multi-step reaction with 10 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

9: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

10: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

With pyridine; sodium hydroxide; 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:

: 118068-41-0,118068-42-1
2,3-di-O-benzyl-6-deoxy-D-arabino-5-hexulofuranose

: 122777-35-9,127304-68-1
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

Guidance literature:: Multi-step reaction with 7 steps

1: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

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

3: 96 percent / pyridine / Ambient temperature

4: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

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

6: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

7: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo00009a009

Reference yield:

: 118068-40-9
(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-ol

: 122777-35-9,127304-68-1
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

Guidance literature:: Multi-step reaction with 8 steps

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

2: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

3: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

4: 96 percent / pyridine / Ambient temperature

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

6: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

7: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

8: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo00009a009