C₇₅H₁₂₉O₁₄Si₃N

Base Information

• Chemical Name: C₇₅H₁₂₉O₁₄Si₃N
• CAS No.: 930803-50-2
• Molecular Formula: C₇₅H₁₂₉NO₁₄Si₃
• Molecular Weight: 1353.1
• Mol file: 930803-50-2.mol

Synonyms:C₇₅H₁₂₉O₁₄Si₃N

Chemical Property of C₇₅H₁₂₉O₁₄Si₃N

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₇₅H₁₂₉O₁₄Si₃N

There total 47 articles about C₇₅H₁₂₉O₁₄Si₃N 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: 80.0%

C79H133O16Si3N (930803-71-7) → C75H129O14Si3N (930803-50-2)

Guidance literature:

With dimedone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/anie.200604053

Reference yield:

C9H15S2Br (930803-23-9) → C75H129O14Si3N (930803-50-2)

Guidance literature:

Multi-step reaction with 18 steps

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

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -78 °C

3.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C

4.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H₂O; methanol / 20 °C

5.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / -5 °C

6.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 20 °C / pH 7

7.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH₂Cl₂

8.1: 82 percent / CrCl₂ / tetrahydrofuran / 0 - 20 °C

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

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

10.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C

11.1: 81 percent / 4-pyrrolidinopyridine / CH₂Cl₂

12.1: 89 percent / lithium hydroxide / H₂O; tetrahydrofuran / 0 °C

13.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

14.1: 66 percent / 2,6-lutidine / CH₂Cl₂ / -20 °C

15.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

16.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C

17.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C

18.1: 80 percent / dimedone / [Pd(PPh₃)4] / tetrahydrofuran / 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; potassium carbonate; dimedone; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 7.1: Swern oxidation;

DOI:10.1002/anie.200604053

Reference yield:

C9H14S2Br2 (930803-27-3) → C75H129O14Si3N (930803-50-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 99 percent / LiBHEt₃ / tetrahydrofuran / 0 °C

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

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -78 °C

4.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C

5.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H₂O; methanol / 20 °C

6.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / -5 °C

7.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 20 °C / pH 7

8.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH₂Cl₂

9.1: 82 percent / CrCl₂ / tetrahydrofuran / 0 - 20 °C

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

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

11.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C

12.1: 81 percent / 4-pyrrolidinopyridine / CH₂Cl₂

13.1: 89 percent / lithium hydroxide / H₂O; tetrahydrofuran / 0 °C

14.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

15.1: 66 percent / 2,6-lutidine / CH₂Cl₂ / -20 °C

16.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

17.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C

18.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C

19.1: 80 percent / dimedone / [Pd(PPh₃)4] / tetrahydrofuran / 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; dimedone; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 8.1: Swern oxidation;

DOI:10.1002/anie.200604053

upstream raw materials:

C₇₉H₁₃₃O₁₆Si₃N

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

C₉H₁₄S₂Br₂

C₉H₁₅S₂Br

Downstream raw materials:

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.