(E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester
• CAS No.: 177854-33-0
• Molecular Formula: C₃₅H₆₂O₆Si₂
• Molecular Weight: 635.045
• Mol file: 177854-33-0.mol

Synonyms:(E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester

Chemical Property of (E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester

There total 1 articles about (E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl 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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxirane-2-carbaldehyde → (E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester (177854-33-0) + (E)-3-[(2R,3R)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 2.) -78 deg C;

DOI:10.1039/CC9960001027

Reference yield:

(E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester (177854-33-0) → (E)-3-[(2S,3S)-3-((1R,2R,3R,4R,5R)-6-Benzyloxy-2,4-dihydroxy-1,3,5-trimethyl-hexyl)-oxiranyl]-acrylic acid ethyl ester (177929-77-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; Yield given;

DOI:10.1039/CC9960001027

Reference yield:

(E)-3-[(2S,3S)-3-((1S,2S,3R,4R,5R)-6-Benzyloxy-1,3,5-trimethyl-2,4-bis-triethylsilanyloxy-hexyl)-oxiranyl]-acrylic acid ethyl ester (177854-33-0) → (E)-(S)-4-((4S,5R,6R)-6-{(S)-1-[(4R,5R,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-2-methyl-pent-2-enoic acid ethyl ester (177600-58-7)

Guidance literature:

Multi-step reaction with 10 steps

1: Bu₄NF / tetrahydrofuran / 0 °C

2: 88 percent / H₂O / 1,2-dichloro-ethane / -30 °C

3: imidazole, DMAP / CH₂Cl₂

4: DIBAL-H / toluene / -78 °C

5: 88 percent / MCPBA / CH₂Cl₂ / -10 °C

6: 1.) (COCl)2, Me₂SO, 2.) NEt₃ / 1.) CH₂Cl₂, -70 deg C

7: tetrahydrofuran

8: 98 percent / Bu₄NF / tetrahydrofuran / 0 °C

9: 89 percent / H₂O / CH₂Cl₂ / -45 °C

10: 86 percent / PPTS / CH₂Cl₂

With 1H-imidazole; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1039/CC9960001027

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

Downstream raw materials:

(E)-3-[(2S,3S)-3-((1R,2R,3R,4R,5R)-6-Benzyloxy-2,4-dihydroxy-1,3,5-trimethyl-hexyl)-oxiranyl]-acrylic acid ethyl ester

(E)-(4R,5R,6S,7S,8R,9R,10R)-11-Benzyloxy-5,7,9-trihydroxy-4,6,8,10-tetramethyl-undec-2-enoic acid ethyl ester

(E)-3-[(2R,3R)-3-((1S,2S,3R,4R,5R,6R,7R)-8-Benzyloxy-2,4,6-trihydroxy-1,3,5,7-tetramethyl-octyl)-oxiranyl]-2-methyl-acrylic acid ethyl ester

(E)-(S)-4-((4S,5R,6R)-6-{(S)-1-[(4R,5R,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-2-methyl-pent-2-enoic acid ethyl ester