INTEMEDIATE FOR MUPIRICIN

Base Information

• Chemical Name: INTEMEDIATE FOR MUPIRICIN
• CAS No.: 75452-45-8
• Molecular Formula: C25H40 O6
• Molecular Weight: 436.589
• Mol file: 75452-45-8.mol

Synonyms:INTEMEDIATE FOR MUPIRICIN

Chemical Property of INTEMEDIATE FOR MUPIRICIN

Chemical Property:

• PSA: 74.22000
• LogP: 4.30850

Purity/Quality:

95% ^*data from raw suppliers

INTEMEDIATE FOR MUPIRICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of INTEMEDIATE FOR MUPIRICIN

There total 15 articles about INTEMEDIATE FOR MUPIRICIN 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) → C25H40O6 (75452-45-8)

Guidance literature:

Multi-step reaction with 14 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.

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; 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) → C25H40O6 (75452-45-8)

Guidance literature:

Multi-step reaction with 15 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.

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; 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) → C25H40O6 (75452-45-8)

Guidance literature:

Multi-step reaction with 13 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.

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; molecular sieve; tetrabutyl ammonium fluoride; iodine; toluene-4-sulfonic acid; copper(II) sulfate; 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:

((2S,3S)-3-hydroxy-2-methylbutyl)triphenylphosphonium iodide

(E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enal

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

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

Downstream raw materials:

pseudomonic acid C

mupirocin