Isopseudomonic acid A

Base Information

• Chemical Name: Isopseudomonic acid A
• CAS No.: 67919-87-3
• Molecular Formula: C₂₆H₄₄O₉
• Molecular Weight: 500.63

Synonyms:

Chemical Property of Isopseudomonic acid A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Isopseudomonic acid A

There total 23 articles about Isopseudomonic acid A 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:

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol (528869-25-2) → mupirocin (12650-69-0,67919-87-3,80558-54-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

2: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

3: 82 percent / xylene / 18 h / Heating

4: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

5: 86 percent / NaBH₄ / ethanol

6: 93 percent / imidazole / dimethylformamide

7: 94 percent / xylene / 7 h / Heating

8: 81 percent / tetrahydrofuran / -78 °C

9: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

10: 93 percent / anhydr. CuSO₄, TsOH

11: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

12: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

13: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

14: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

15: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

Reference yield:

D-Arabinose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) → mupirocin (12650-69-0,67919-87-3,80558-54-9)

Guidance literature:

Multi-step reaction with 17 steps

1: HBr, Ac₂O

2: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

3: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

4: 82 percent / xylene / 18 h / Heating

5: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

6: 86 percent / NaBH₄ / ethanol

7: 93 percent / imidazole / dimethylformamide

8: 94 percent / xylene / 7 h / Heating

9: 81 percent / tetrahydrofuran / -78 °C

10: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

11: 93 percent / anhydr. CuSO₄, TsOH

12: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

13: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

14: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

15: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

16: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; hydrogen bromide; hydrogen; iodine; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

Reference yield:

1,5-Anhydro-D-arabinitol (32742-34-0) → mupirocin (12650-69-0,67919-87-3,80558-54-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

2: 82 percent / xylene / 18 h / Heating

3: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

4: 86 percent / NaBH₄ / ethanol

5: 93 percent / imidazole / dimethylformamide

6: 94 percent / xylene / 7 h / Heating

7: 81 percent / tetrahydrofuran / -78 °C

8: 85 percent / N-Methylmorpholine-N-oxide, OsO₄

9: 93 percent / anhydr. CuSO₄, TsOH

10: 75 percent / tetrahydrofuran / 24 h / Ambient temperature

11: 87 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

12: 80 percent / PCC,molecular sieve / CH₂Cl₂ / 1 h / Ambient temperature

13: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min.

14: 50percent aq. AcOH / 72 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; iodine; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; 4-methylmorpholine N-oxide; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

upstream raw materials:

Ethyl monate C

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol

(3S,4S)-3-(2-Hydroxy-ethyl)-3,4-dihydro-2H-pyran-4-ol

(3S,4S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4-dihydro-2H-pyran-4-ol

Downstream raw materials:

pseudomonic acid C

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