1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone

Base Information

• Chemical Name: 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone
• CAS No.: 160388-98-7
• Molecular Formula: C₆₃H₁₀₉NO₁₃Si₂
• Molecular Weight: 1144.73

Synonyms:1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone

Chemical Property of 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone

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Technology Process of 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone

There total 4 articles about 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.0^4,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone 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: 30.0%

32(R)-hydroxy-28,40-bis(triethylsilyl)rapamycin (160496-10-6) → 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.04,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone (160388-98-7)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃;

DOI:10.1016/S0960-894X(98)00735-5

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.04,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone (160388-98-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂

2: 30 percent / L-selectride / tetrahydrofuran / -78 °C

3: 30 percent / K₂CO₃ / methanol / 0 - 20 °C

With 2,6-dimethylpyridine; L-Selectride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(98)00735-5

Reference yield:

sirolimus (53123-88-9) → 1-hydroxy-12-[2-hydroxy-4-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-3-methyl-butyl]-17,28-dimethoxy-13,15,19,21,27,33-hexamethyl-16-triethylsilanyloxy-11,34-dioxa-4-aza-tricyclo[28.3.1.04,9]tetratriaconta-14,22,24,26-tetraene-2,3,10,18-tetraone (160388-98-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂

2: 30 percent / L-selectride / tetrahydrofuran / -78 °C

3: 30 percent / K₂CO₃ / methanol / 0 - 20 °C

With 2,6-dimethylpyridine; L-Selectride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(98)00735-5

upstream raw materials:

32(R)-hydroxy-28,40-bis(triethylsilyl)rapamycin

triethylsilyl trifluoromethyl sulfonate

sirolimus

31,42-bis(triethylsilylether)rapamycin

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