C₇₉H₁₃₃O₁₆Si₃N

Base Information

• Chemical Name: C₇₉H₁₃₃O₁₆Si₃N
• CAS No.: 930803-49-9
• Molecular Formula: C₇₉H₁₃₃NO₁₆Si₃
• Molecular Weight: 1437.18
• Mol file: 930803-49-9.mol

Synonyms:C₇₉H₁₃₃O₁₆Si₃N

Chemical Property of C₇₉H₁₃₃O₁₆Si₃N

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₇₉H₁₃₃O₁₆Si₃N

There total 52 articles about C₇₉H₁₃₃O₁₆Si₃N 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: 81.0%

C79H134O16Si3NBr (930803-74-0) → C79H133O16Si3N (930803-49-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/anie.200604053

Reference yield:

C10H15S2O2Br (930803-25-1) → C79H133O16Si3N (930803-49-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 99 percent / diisobutylaluminum hydride / CH₂Cl₂ / -45 °C

2.1: 70 percent / methanesulfonyl chloride; triethylamine; 4-(dimethylamino)pyridine / lithium bromide / CH₂Cl₂; dimethylformamide

3.1: 99 percent / LiBHEt₃ / tetrahydrofuran / 0 °C

4.1: tert-butyllithium / tetrahydrofuran / -96 - -78 °C

5.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -78 °C

6.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C

7.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H₂O; methanol / 20 °C

8.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / -5 °C

9.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 20 °C / pH 7

10.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH₂Cl₂

11.1: 82 percent / CrCl₂ / tetrahydrofuran / 0 - 20 °C

12.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl₂]; hexamethyltin / 20 °C

12.2: [Pd{P(2-furyl)3}2Cl₂]; N-methylpyrrolidinone / 20 °C

13.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C

14.1: 81 percent / 4-pyrrolidinopyridine / CH₂Cl₂

15.1: 89 percent / lithium hydroxide / H₂O; tetrahydrofuran / 0 °C

16.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

17.1: 66 percent / 2,6-lutidine / CH₂Cl₂ / -20 °C

18.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

19.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; oxalyl dichloride; tert.-butyl lithium; hexamethyldistannane; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; methanesulfonyl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 10.1: Swern oxidation;

DOI:10.1002/anie.200604053

Reference yield:

C9H15S2OBr (930803-26-2) → C79H133O16Si3N (930803-49-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 70 percent / methanesulfonyl chloride; triethylamine; 4-(dimethylamino)pyridine / lithium bromide / CH₂Cl₂; dimethylformamide

2.1: 99 percent / LiBHEt₃ / tetrahydrofuran / 0 °C

3.1: tert-butyllithium / tetrahydrofuran / -96 - -78 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -78 °C

5.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C

6.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H₂O; methanol / 20 °C

7.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / -5 °C

8.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 20 °C / pH 7

9.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH₂Cl₂

10.1: 82 percent / CrCl₂ / tetrahydrofuran / 0 - 20 °C

11.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl₂]; hexamethyltin / 20 °C

11.2: [Pd{P(2-furyl)3}2Cl₂]; N-methylpyrrolidinone / 20 °C

12.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C

13.1: 81 percent / 4-pyrrolidinopyridine / CH₂Cl₂

14.1: 89 percent / lithium hydroxide / H₂O; tetrahydrofuran / 0 °C

15.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

16.1: 66 percent / 2,6-lutidine / CH₂Cl₂ / -20 °C

17.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

18.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; oxalyl dichloride; tert.-butyl lithium; hexamethyldistannane; lithium triethylborohydride; potassium carbonate; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; methanesulfonyl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 9.1: Swern oxidation;

DOI:10.1002/anie.200604053

upstream raw materials:

C₇₉H₁₃₄O₁₆Si₃NBr

(2R,4S)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanal

C₉H₁₄S₂Br₂

C₉H₁₅S₂Br

Downstream raw materials:

C₇₉H₁₃₃O₁₆Si₃N

C₇₅H₁₂₉O₁₄Si₃N

C₆₉H₁₂₁O₁₃Si₃N

sirolimus

Refernces

• 1、 Maddess, Matthew L.,Tackett, Miles N.,Watanabe, Hidenori,Brennan, Paul E.,Spilling, Christopher D.,Scott, James S.,Osborn, David P.,Ley, Steven V.. "Total synthesis of rapamycin". . p. 591 - 597. Retrieved 2008/02/01.