9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid

Base Information

• Chemical Name: 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid
• CAS No.: 262279-42-5
• Molecular Formula: C₆₆H₉₁N₃O₁₆Si
• Molecular Weight: 1210.54
• Mol file: 262279-42-5.mol

Synonyms:9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid

Chemical Property of 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid

There total 37 articles about 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid 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: 65.0%

C72H105N3O16Si2 (262279-36-7) → 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid (262279-42-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 50 ℃; for 22h;

DOI:10.1021/ja994003r

Reference yield:

2''-(tert-Butyl-diphenyl-silanyloxymethyl)-[2,4';2',4'']teroxazole-4-carbaldehyde (194232-63-8) → 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid (262279-42-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 65 percent / TiCl₄ / CH₂Cl₂ / 24 h / -78 - 20 °C

2.1: 93 percent / silver(I) oxide / 10 h / Heating

3.1: OsO₄; trimethylamine N-oxide dihydrate; t-BuOH / tetrahydrofuran; H₂O; toluene / 4 h / 20 °C

4.1: 773 mg / Pb(OAc)4; K₂CO₃ / diethyl ether / 0.25 h / 0 °C

5.1: 80 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylformamide / 20 °C

6.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 94 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

8.1: 92 percent / CBr₄; PPh₃; 2,6-lutidine / dimethylformamide / 0.5 h

9.1: TFA / CH₂Cl₂ / 3 h / 0 °C

10.1: triethylphosphine / dimethylformamide / 0.5 h / 20 °C

10.2: 86 percent / DBU / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C

11.1: 65 percent / PPTS / ethanol / 22 h / 50 °C

With pyridine; 2,6-dimethylpyridine; chromium dichloride; lead(IV) acetate; osmium(VIII) oxide; carbon tetrabromide; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; trifluoroacetic acid; nickel dichloride; silver(l) oxide; tert-butyl alcohol; triethylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6.1: Dess-Martin oxidation / 10.1: Schlosser-Wittig olefination;

DOI:10.1021/ja002377a

Reference yield:

2,2-Dimethyl-propionic acid (3S,4R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-7-oxo-heptyl ester → 9-{2''-[14-acetoxy-16-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-hydroxy-4,8-dimethoxy-5,9,13,15-tetramethyl-12-oxo-hexadec-1-enyl]-[2,4';2',4'']teroxazol-4-yl}-3-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-8-methyl-7-oxo-non-5-enoic acid (262279-42-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 88 percent / TiCl₄ / CH₂Cl₂ / 8 h / -78 °C

2.1: 87 percent / Proton Sponge(R) / CH₂Cl₂ / 15 h / 0 - 25 °C

3.1: O₃; pyridine / methanol / 0.17 h / -78 °C

3.2: methylsulfide / methanol / 10 h / 25 °C

4.1: 1.18 g / CrCl₂ / tetrahydrofuran / 20 °C

5.1: 88 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 20 °C

6.1: NaNO₂; H₂ / PtO₂ / ethyl acetate; ethanol / 3 h / 3040.2 Torr

7.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

8.1: 411 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.5 h / 20 °C

9.1: 87 percent / aq. DDQ / CH₂Cl₂ / 0.75 h / 20 °C

10.1: 82 percent / DMAP / CH₂Cl₂ / 0.5 h / 0 °C

11.1: triethylphosphine / dimethylformamide / 0.5 h / 20 °C

11.2: 86 percent / DBU / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C

12.1: 65 percent / PPTS / ethanol / 22 h / 50 °C

With pyridine; chromium dichloride; dmap; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; Dess-Martin periodane; ozone; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; sodium nitrite; triethylphosphine; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 4.1: Takai olefination / 11.1: Schlosser-Wittig olefination;

DOI:10.1021/ja002377a

upstream raw materials:

C₇₂H₁₀₅N₃O₁₆Si₂

2''-(tert-Butyl-diphenyl-silanyloxymethyl)-[2,4';2',4'']teroxazole-4-carbaldehyde

(5S,6S)-(E)-methyl 6-methoxy-5-methyl-6-(2-tert-butyldiphenylsiloxymethyl-2,4'-trisoxazole-4'-yl)-hex-3-enoate

(S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate

Downstream raw materials:

C₆₃H₈₂N₄O₁₄Si

C₆₆H₈₉N₃O₁₅Si