(E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

Base Information

• Chemical Name: (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone
• CAS No.: 173007-24-4
• Molecular Formula: C₄₃H₆₈N₄O₁₀
• Molecular Weight: 801.034

Synonyms:(E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

Chemical Property of (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

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Technology Process of (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-tetraone

There total 3 articles about (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-ene-2,3,10,16-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:

C49H72N2O15S → (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (173007-24-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/S0960-894X(97)00409-5

Reference yield:

ascomycin (135635-46-0,137767-76-1,104987-12-4,133876-12-7) → (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (173007-24-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pTsOH, 2.) H₂ / 2.) Rh/C / 1.) benzene, 60 deg C, 2.) EtOH

2: Et₃N, DMAP / CH₂Cl₂

3: NaN₃ / dimethylformamide / 60 °C

With dmap; sodium azide; hydrogen; toluene-4-sulfonic acid; triethylamine; Rh on carbon; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00409-5

Reference yield:

33-(tert-butyldimethylsilyl)-24-deoxy-ascomycin (134226-79-2) → (E)-(1R,9S,12S,13R,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4S)-4-Azido-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (173007-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂

2: NaN₃ / dimethylformamide / 60 °C

With dmap; sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00409-5

upstream raw materials:

ascomycin

33-(tert-butyldimethylsilyl)-24-deoxy-ascomycin

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