(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide

Base Information

• Chemical Name: (E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide
• CAS No.: 116386-70-0
• Molecular Formula: C₅₃H₁₀₉NO₇Si₄
• Molecular Weight: 984.793
• Mol file: 116386-70-0.mol

Synonyms:(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide

Chemical Property of (E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide

There total 1 articles about (E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide 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:

t-butyldimethylsiyl triflate (69739-34-0) + methylchloroaluminium N-methoxy-N-methylamide (116386-59-5) + (S)-3-[(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-hydroxy-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoyl]-4-isopropyl-oxazolidin-2-one (116386-69-7) → (E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide (116386-70-0)

Guidance literature:

With 2,6-dimethylpyridine; Multistep reaction; 1.) CH₂Cl₂, -20 deg C to 22 deg C, 12 h; 2.) CH₂Cl₂, 0 deg C;

DOI:10.1016/S0040-4039(00)80074-X

Reference yield: 98.0%

(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide (116386-70-0) → (E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enal (118949-48-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -30 ℃;

DOI:10.1021/ja00185a071

Reference yield:

(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoic acid methoxy-methyl-amide (116386-70-0) → C80H155NO11S2Si4 (126789-44-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / DIBAl / tetrahydrofuran / -30 °C

2: 1.) n-Buli, 2.) KHMDS / 1.) THF, -78 deg C, 2.) THF, O deg C

3: TFA / tetrahydrofuran; H₂O / 20 °C

4: DCC, DMAP / CH₂Cl₂ / -15 °C

With dmap; n-butyllithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja00185a071

upstream raw materials:

t-butyldimethylsiyl triflate

methylchloroaluminium N-methoxy-N-methylamide

(S)-3-[(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-hydroxy-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enoyl]-4-isopropyl-oxazolidin-2-one

Downstream raw materials:

(E)-(2S,3R,5S,6R,7S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-9-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-6,8-dimethyl-7-triethylsilanyloxy-5-triisopropylsilanyloxy-non-8-enal

C₇₅H₁₅₂O₈S₂Si₅

C₆₉H₁₃₈O₈S₂Si₄

C₈₀H₁₅₅NO₁₁S₂Si₄