33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50

Base Information

• Chemical Name: 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50
• CAS No.: 134590-89-9
• Molecular Formula: C₅₃H₉₁NO₁₂Si₂
• Molecular Weight: 990.476
• Mol file: 134590-89-9.mol

Synonyms:33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50

Chemical Property of 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50

There total 6 articles about 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50 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: 69.0%

33-O-tert.butyldimethylsilyl-22(S)-dihydro-26-O-trimethylsilyl-iso-FK-506 (134556-85-7) → 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50 (134590-89-9)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; for 12h; Ambient temperature; presence of 4 A mol sieve;

DOI:10.1016/S0040-4020(01)89004-9

Reference yield:

Tacrolimus (104987-11-3) → 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50 (134590-89-9)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / dimethylformamide

2: 66 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 5 h / -5 - 0 °C

3: 70 percent / 4-dimethylaminopyridine / dimethylformamide / 168 h / 50 °C

4: 57 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -70 °C

5: 69 percent / N-methyl-morpholine-N-oxide, tetrapropylammonium-perrhutenate / CH₂Cl₂ / 12 h / Ambient temperature; presence of 4 A mol sieve

With 1H-imidazole; 2,6-dimethylpyridine; dmap; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)89004-9

Reference yield:

33-O-tert.butyldimethylsilyl-FK-506 (104987-25-9) → 33-O-tert.butyldimethylsilyl-26-O-trimethylsilyl-iso-FK-50 (134590-89-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 5 h / -5 - 0 °C

2: 70 percent / 4-dimethylaminopyridine / dimethylformamide / 168 h / 50 °C

3: 57 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -70 °C

4: 69 percent / N-methyl-morpholine-N-oxide, tetrapropylammonium-perrhutenate / CH₂Cl₂ / 12 h / Ambient temperature; presence of 4 A mol sieve

With 2,6-dimethylpyridine; dmap; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)89004-9

upstream raw materials:

33-O-tert.butyldimethylsilyl-22(S)-dihydro-26-O-trimethylsilyl-iso-FK-506

Tacrolimus

33-O-tert.butyldimethylsilyl-FK-506

tert-butyldimethylsilyl chloride

Downstream raw materials:

iso-FK-506

Refernces