methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate

Base Information

• Chemical Name: methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate
• CAS No.: 243469-77-4
• Molecular Formula: C₂₃H₃₁NO₆SSi
• Molecular Weight: 477.654

Synonyms:methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate

Chemical Property of methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate

Chemical Property:

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Technology Process of methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate

There total 12 articles about methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate 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: 97.0%

phenylcarbonochloridothioate (1005-56-7) + methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxy-pyrid-4-yl>-2-hydroxyethanoate (243469-75-2) → methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate (243469-77-4)

Guidance literature:

With pyridine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1002/jhet.5570360313

Reference yield:

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate (243469-77-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 2.) H₂ / 2.) 10 percent Pd/C / 1.) MeOH, from 20 deg C to 40 deg C, 30 min, 2.) MeOH, 50 psi, 3 h

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

3: Et₃N / tetrahydrofuran / 0.5 h

4: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 0.5 h / Ambient temperature

5: 90 percent / DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

6: 89 percent / NaBH₄ / methanol / 1 h / 0 °C

7: 96 percent / imidazole / dimethylformamide / Ambient temperature

8: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, from -78 deg C, to RT

9: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 15 min

10: 71 percent / HgCl₂, HgO / H₂O / 4 h / Ambient temperature

11: 97 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; hydrogen; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570360313

Reference yield:

2-chloro-4-methyl-3-pyridinecarbonitrile (65169-38-2) → methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxypyrid-4-yl>-2-<(phenoxy)thiocarbonyloxy>ethanoate (243469-77-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / methanol / 1 h / Heating

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

3: Et₃N / tetrahydrofuran / 0.5 h

4: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 0.5 h / Ambient temperature

5: 90 percent / DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

6: 89 percent / NaBH₄ / methanol / 1 h / 0 °C

7: 96 percent / imidazole / dimethylformamide / Ambient temperature

8: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, from -78 deg C, to RT

9: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 15 min

10: 71 percent / HgCl₂, HgO / H₂O / 4 h / Ambient temperature

11: 97 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570360313

upstream raw materials:

phenylcarbonochloridothioate

methyl 2-<3-<<<(1,1-dimethylthyl)dimethylsilyl>oxy>methyl>-2-methoxy-pyrid-4-yl>-2-hydroxyethanoate

2-chloro-4-methyl-3-pyridinecarbonitrile

2,6-dichloro-4-methylnicotinonitrile

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