(E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,3,4,11,17-pentaone

Base Information

• Chemical Name: (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,3,4,11,17-pentaone
• CAS No.: 242125-87-7
• Molecular Formula: C₄₃H₆₇NO₁₂
• Molecular Weight: 790.004

Synonyms:(E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,3,4,11,17-pentaone

Chemical Property of (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,3,4,11,17-pentaone

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Technology Process of (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,3,4,11,17-pentaone

There total 3 articles about (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,3,4,11,17-pentaone 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: 87.0%

15-(tert-butyl-dimethyl-silanyloxy)-13-{2-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-18-ethyl-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.05,10]octacos-19-ene-2,3,4,11,17-pentaone → (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.05,10]octacos-19-ene-2,3,4,11,17-pentaone (242125-87-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 7h; Ambient temperature;

DOI:10.1055/s-1999-3096

Reference yield:

24,33-bis-OTBDMS-ascomycin (137071-45-5) → (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.05,10]octacos-19-ene-2,3,4,11,17-pentaone (242125-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 37 percent / Ph₃PI₂, imidazole / acetonitrile / 15 h / Heating

2: 72 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 15 h / Ambient temperature

3: 87 percent / HF / acetonitrile / 7 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogen fluoride; Dess-Martin periodane; triphenylphospine diiodide; In dichloromethane; acetonitrile;

DOI:10.1055/s-1999-3096

Reference yield:

15-(tert-butyl-dimethyl-silanyloxy)-13-{2-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-18-ethyl-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.05,10]octacos-19-ene-2,4,11,17-tetraone (1053509-37-7) → (E)-(1R,10S,13S,14R,15S,18R,22S,24S,25R,26S)-18-Ethyl-15-hydroxy-13-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.05,10]octacos-19-ene-2,3,4,11,17-pentaone (242125-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 15 h / Ambient temperature

2: 87 percent / HF / acetonitrile / 7 h / Ambient temperature

With pyridine; hydrogen fluoride; Dess-Martin periodane; In dichloromethane; acetonitrile;

DOI:10.1055/s-1999-3096

upstream raw materials:

24,33-bis-OTBDMS-ascomycin

15-(tert-butyl-dimethyl-silanyloxy)-13-{2-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-18-ethyl-24,26-dimethoxy-1,14,20,22-tetramethyl-12,28-dioxa-5-aza-tricyclo[23.2.1.0^5,10]octacos-19-ene-2,4,11,17-tetraone

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