12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone

Base Information

• Chemical Name: 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone
• CAS No.: 142498-46-2
• Molecular Formula: C₄₉H₈₁NO₁₁Si
• Molecular Weight: 888.268

Synonyms:12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone

Chemical Property of 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone

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Technology Process of 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone

There total 1 articles about 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-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:

33-O-(tert-butyldimethylsilyl)-ascomycin (133941-74-9) → 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone (142498-46-2)

Guidance literature:

With dmap; methanesulfonyl chloride;

DOI:10.1016/S0040-4020(00)00669-4

Reference yield: 55.0%

triethylsilane (617-86-7) + 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone (142498-46-2) → 33-(tert-butyldimethylsilyl)-24-deoxy-ascomycin (134226-79-2) + 33-(tert-butyldimethylsilyl)-24-deoxy-22-dihydro-22-triethylsilyl enol ether ascomycin (307953-32-8)

Guidance literature:

With Wilkinson's catalyst; In benzene; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(00)00669-4

Reference yield: 30.0%

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + 12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-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]octacosa-14,18-diene-2,3,10,16-tetraone (142498-46-2) → (12-{2-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-17-ethyl-1,16-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10-trioxo-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacosa-14,18-dien-16-yl)-acetic acid methyl ester + C58H101NO13Si2

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - -30 ℃; for 3h;

DOI:10.1016/S0040-4020(00)00669-4

upstream raw materials:

33-O-(tert-butyldimethylsilyl)-ascomycin

Downstream raw materials:

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

33-(tert-butyldimethylsilyl)-24-deoxy-22-dihydro-22-triethylsilyl enol ether ascomycin

C₅₈H₁₀₁NO₁₃Si₂

33-(tert-butyldimethylsilyl)-24-deoxy-23-(1-hydroxy-ethyl)-ascomycin

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