(6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS No.: 73973-65-6
• Molecular Formula: C₄₄H₄₄N₆O₁₀S
• Molecular Weight: 848.934

Synonyms:

Chemical Property of (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 20 articles about (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl 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:

(6R,7R)-7-Amino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73910-52-8) + 4-(4-methoxybenzyloxy)benzene malonic acid-4-methoxybenzyl monoester (70175-90-5) → (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73973-65-6)

Guidance literature:

With pyridine; trichlorophosphate; In dichloromethane; at -25 ℃; for 0.25h;

DOI:10.1248/cpb.28.1563

Reference yield:

penicillin-V β-sulfoxide benzyl ester (4052-69-1) → (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73973-65-6)

Guidance literature:

Multi-step reaction with 20 steps

1: 131 g / trimethylphosphite, molecular sieves / toluene / 2 h / Heating

2: 48 g / 0.5N HCl / methanol / 0.25 h / Heating

3: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

4: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

5: Et₃N / CH₂Cl₂ / -78 °C

6: 10 g / Et₃N / 2 h / Ambient temperature

7: Zn / CH₂Cl₂; acetic acid

8: 2.3 g / pyridine / 0.17 h

9: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

10: 17.4 g / n-BuLi / tetrahydrofuran; hexane / 6 h / Ambient temperature

11: 11.8 g / CrO₃ / acetone / 0.25 h / Ambient temperature

12: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C, 40 min

13: SOCl₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

14: 8.81 g / CH₂Cl₂ / 1 h / Heating

15: 60 percent / dioxane / 10 h / Heating

16: 1.) PCl₅, 2.) MeOH, 3.) H₂O / 1.) CH₂Cl₂, pyridine, -25 deg C to r.t., 30 min, 2.) -30 deg C, 20 min, 3.) -20 deg C, 10 min; r.t., 30 min

17: 2.) nickel peroxide / 1.) CH₂Cl₂, reflux, 1 h, 2.) CH₂Cl₂, -20 to 0 deg C, 50 min, 0 deg C, 1 h

18: 388 mg / CH₂Cl₂ / 1.) ice-cooling, overnight, 2.) r.t., 4 h

19: 340 mg / Girard's T reagent / methanol / 1.) r.t., 5 h, 2.) 0 deg C, overnight

20: 200 mg / POCl₃, pyridine / CH₂Cl₂ / 0.25 h / -25 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; nickel(IV) oxide; n-butyllithium; thionyl chloride; molecular sieve; 4 A molecular sieve; phosphorus pentachloride; water; girard's reagent T; sodium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid; acetone; toluene;

DOI:10.1248/cpb.28.1563

Reference yield:

(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester (68047-66-5) → (6R,7R)-7-Methoxy-7-{2-(4-methoxy-benzyloxycarbonyl)-2-[4-(4-methoxy-benzyloxy)-phenyl]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (73973-65-6)

Guidance literature:

Multi-step reaction with 18 steps

1: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

2: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

3: Et₃N / CH₂Cl₂ / -78 °C

4: 10 g / Et₃N / 2 h / Ambient temperature

5: Zn / CH₂Cl₂; acetic acid

6: 2.3 g / pyridine / 0.17 h

7: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

8: 17.4 g / n-BuLi / tetrahydrofuran; hexane / 6 h / Ambient temperature

9: 11.8 g / CrO₃ / acetone / 0.25 h / Ambient temperature

10: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C, 40 min

11: SOCl₂, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

12: 8.81 g / CH₂Cl₂ / 1 h / Heating

13: 60 percent / dioxane / 10 h / Heating

14: 1.) PCl₅, 2.) MeOH, 3.) H₂O / 1.) CH₂Cl₂, pyridine, -25 deg C to r.t., 30 min, 2.) -30 deg C, 20 min, 3.) -20 deg C, 10 min; r.t., 30 min

15: 2.) nickel peroxide / 1.) CH₂Cl₂, reflux, 1 h, 2.) CH₂Cl₂, -20 to 0 deg C, 50 min, 0 deg C, 1 h

16: 388 mg / CH₂Cl₂ / 1.) ice-cooling, overnight, 2.) r.t., 4 h

17: 340 mg / Girard's T reagent / methanol / 1.) r.t., 5 h, 2.) 0 deg C, overnight

18: 200 mg / POCl₃, pyridine / CH₂Cl₂ / 0.25 h / -25 °C

With pyridine; chromium(VI) oxide; methanol; nickel(IV) oxide; n-butyllithium; thionyl chloride; 4 A molecular sieve; phosphorus pentachloride; water; girard's reagent T; sodium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid; acetone;

DOI:10.1248/cpb.28.1563

upstream raw materials:

(6R,7R)-7-Amino-7-methoxy-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

4-(4-methoxybenzyloxy)benzene malonic acid-4-methoxybenzyl monoester

penicillin-V β-sulfoxide benzyl ester

(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester

Downstream raw materials:

7β-<2-(4-hydroxy)phenyl-2-carboxy>acetylamino-7α-methoxy-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-1-carba-1-dethia-3-cephem-4-carboxylic acid

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