Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester

Base Information

• Chemical Name: Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester
• CAS No.: 155351-82-9
• Molecular Formula: C₄₁H₃₉NO₁₅Se
• Molecular Weight: 864.718

Synonyms:Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester

Chemical Property of Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester

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Technology Process of Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester

There total 15 articles about Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl 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:

5-bromo-3-methoxysalicylaldehyde (5034-74-2) → Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester (155351-82-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 87.8 percent / K₂CO₃ / ethanol / 3 h / Heating

2: 99.7 percent / TsOH*H₂O / benzene / 1 h / Heating

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, Et₂O, from -78 deg C to 0 deg C, 2 h

4: 99.5 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

5: 2.08 g / HCO₂NH₄, 10percent Pd/C / methanol / 0.17 h / Ambient temperature

6: 2.59 g / i-Pr₂NEt / CH₂Cl₂ / 0.17 h / -78 °C

7: 8 N aq. H₂SO₄ / tetrahydrofuran / 2 h / 50 °C

8: i-Pr₂NEt / CH₂Cl₂ / 36 h / Ambient temperature

9: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / acetone / 0.5 h / Ambient temperature

10: 82.5 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCI), DMAP / diethyl ether / 11 h / Ambient temperature

11: 65.2 percent / (Ph₃P)2PdCl₂, sodium pivalate / N,N-dimethyl-acetamide / 1 h / 80 °C

12: Raney Ni, H₂ / ethanol / 60 h / 760 Torr / Ambient temperature

13: pyridine, DMAP / 5 h / Ambient temperature

14: 93.5 percent / (TMS)Br / CH₂Cl₂ / 5 h / -78 - -10 °C

15: n-Bu₃P / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium chlorite; sodium dihydrogenphosphate; palladium on activated charcoal; n-butyllithium; 2-methyl-but-2-ene; trimethylsilyl bromide; tributylphosphine; sulfuric acid; hydrogen; ammonium formate; nickel; sodium pivalate; potassium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl acetamide; acetone; benzene;

DOI:10.1021/ja00082a023

Reference yield:

2-O-benzyl-5-bromo-2-hydroxy-3-methoxybenzaldehyde (155351-68-1) → Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester (155351-82-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 99.7 percent / TsOH*H₂O / benzene / 1 h / Heating

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, Et₂O, from -78 deg C to 0 deg C, 2 h

3: 99.5 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

4: 2.08 g / HCO₂NH₄, 10percent Pd/C / methanol / 0.17 h / Ambient temperature

5: 2.59 g / i-Pr₂NEt / CH₂Cl₂ / 0.17 h / -78 °C

6: 8 N aq. H₂SO₄ / tetrahydrofuran / 2 h / 50 °C

7: i-Pr₂NEt / CH₂Cl₂ / 36 h / Ambient temperature

8: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / acetone / 0.5 h / Ambient temperature

9: 82.5 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCI), DMAP / diethyl ether / 11 h / Ambient temperature

10: 65.2 percent / (Ph₃P)2PdCl₂, sodium pivalate / N,N-dimethyl-acetamide / 1 h / 80 °C

11: Raney Ni, H₂ / ethanol / 60 h / 760 Torr / Ambient temperature

12: pyridine, DMAP / 5 h / Ambient temperature

13: 93.5 percent / (TMS)Br / CH₂Cl₂ / 5 h / -78 - -10 °C

14: n-Bu₃P / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium chlorite; sodium dihydrogenphosphate; palladium on activated charcoal; n-butyllithium; 2-methyl-but-2-ene; trimethylsilyl bromide; tributylphosphine; sulfuric acid; hydrogen; ammonium formate; nickel; sodium pivalate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl acetamide; acetone; benzene;

DOI:10.1021/ja00082a023

Reference yield:

2-hydroxy-3-methoxy-5-<5-(methoxymethoxy)ethyl>benzaldehyde trimethylene acetal (155351-72-7) → Acetic acid 4-[(2R,3S,4S,5S)-3,4-diacetoxy-5-((R)-1-acetoxy-ethyl)-tetrahydro-furan-2-yl]-10,12-dimethoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester (155351-82-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 2.59 g / i-Pr₂NEt / CH₂Cl₂ / 0.17 h / -78 °C

2: 8 N aq. H₂SO₄ / tetrahydrofuran / 2 h / 50 °C

3: i-Pr₂NEt / CH₂Cl₂ / 36 h / Ambient temperature

4: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / acetone / 0.5 h / Ambient temperature

5: 82.5 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDCI), DMAP / diethyl ether / 11 h / Ambient temperature

6: 65.2 percent / (Ph₃P)2PdCl₂, sodium pivalate / N,N-dimethyl-acetamide / 1 h / 80 °C

7: Raney Ni, H₂ / ethanol / 60 h / 760 Torr / Ambient temperature

8: pyridine, DMAP / 5 h / Ambient temperature

9: 93.5 percent / (TMS)Br / CH₂Cl₂ / 5 h / -78 - -10 °C

10: n-Bu₃P / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilyl bromide; tributylphosphine; sulfuric acid; hydrogen; nickel; sodium pivalate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl acetamide; acetone;

DOI:10.1021/ja00082a023

upstream raw materials:

ortho-nitrophenyl selenocyanate

1-acetoxy-8-(2-hydroxyethyl)-10,12-dimethoxy-4-(2,3,5-tri-O-acetyl-α-D-fucofuranosyl)-6H-benzonaphtho<1,2-b>pyran-6-one

5-bromo-3-methoxysalicylaldehyde

2-O-benzyl-5-bromo-2-hydroxy-3-methoxybenzaldehyde

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