14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-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: 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-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.: 146096-65-3
• Molecular Formula: C₅₇H₈₉NO₁₃Si
• Molecular Weight: 1024.42
• Mol file: 146096-65-3.mol

Synonyms:

Chemical Property of 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-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 6 articles about 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-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:

14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-12-{2-[4-(2-hydroxy-2-phenyl-ethoxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-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 → 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (146096-65-3)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane;

DOI:10.1016/S0960-894X(99)00335-2

Reference yield:

phenylmagnesium bromide (100-58-3) → 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (146096-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / tetrahydrofuran / -78 °C

2: TPAP, 4-methylmorpholine N-oxide, 4 Angstroem sieves / CH₂Cl₂

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0960-894X(99)00335-2

Reference yield:

24-O-tert-butyldimethylsilyl-ascomycin (137820-27-0) → 14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-12-{2-[3-methoxy-4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-1-methyl-vinyl}-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (146096-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TfOH / cyclohexane; CH₂Cl₂

2: 1.) OsO₄, NMO, 2.) NaIO₄

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; In dichloromethane; cyclohexane;

DOI:10.1016/S0960-894X(99)00335-2

upstream raw materials:

phenylmagnesium bromide

24-O-tert-butyldimethylsilyl-ascomycin

C₅₁H₈₅NO₁₃Si

2,2,2-trichloro-acetimidic acid 2-phenyl-allyl ester