formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester

Base Information

• Chemical Name: formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester
• CAS No.: 649748-37-8
• Molecular Formula: C₅₀H₈₃NO₁₃Si
• Molecular Weight: 934.293

Synonyms:formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester

Chemical Property of formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester

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Technology Process of formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester

There total 3 articles about formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.0^4,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester 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: 88.0%

formyl acetic anhydride (2258-42-6) + 24-O-tert-butyldimethylsilyl-ascomycin (137820-27-0) → formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester (649748-37-8)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tet.2003.10.045

Reference yield:

ascomycin (135635-46-0,137767-76-1,104987-12-4,133876-12-7) → formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester (649748-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide

2: 95 percent / HF / acetonitrile; H₂O / 0.25 h

3: 88 percent / DMAP / acetonitrile / 20 °C

With 1H-imidazole; dmap; hydrogen fluoride; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tet.2003.10.045

Reference yield:

24,33-bis-OTBDMS-ascomycin (137071-45-5) → formic acid 4-{2-[14-(tert-butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-en-12-yl]-propenyl}-2-methoxy-cyclohexyl ester (649748-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / HF / acetonitrile; H₂O / 0.25 h

2: 88 percent / DMAP / acetonitrile / 20 °C

With dmap; hydrogen fluoride; In water; acetonitrile;

DOI:10.1016/j.tet.2003.10.045

upstream raw materials:

formyl acetic anhydride

24-O-tert-butyldimethylsilyl-ascomycin

ascomycin

24,33-bis-OTBDMS-ascomycin

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