(E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester
• CAS No.: 917079-01-7
• Molecular Formula: C₃₇H₅₀O₅Si
• Molecular Weight: 602.886
• Mol file: 917079-01-7.mol

Synonyms:(E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester

Chemical Property of (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester

There total 10 articles about (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic 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: 98.0%

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate (917078-95-6) + triisopropylsilyl methanesulfonate → (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester (917079-01-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal (917078-93-4) → (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester (917079-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / CH₂Cl₂ / 2 h / 20 °C

2: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

3: 98 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; potassium carbonate; In ethanol; dichloromethane; 1: Wittig olefination;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formyloxy-6-phenyl-2-hexenoate → (E)-(4R,5S,6R)-4,6-Bis-benzyloxy-6-phenyl-5-triisopropylsilanyloxy-hex-2-enoic acid ethyl ester (917079-01-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / K₂CO₃ / ethanol / 1 h / 20 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

With 2,6-dimethylpyridine; potassium carbonate; In ethanol; dichloromethane;

DOI:10.1016/j.tet.2006.09.005

upstream raw materials:

(4R,5S,6R)-ethyl-4,6-bis(benzyloxy)-5-formiloxy-5-phenyl-(2E)-hexenoate

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal

((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanol

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

Downstream raw materials:

(4S,5R)-ethyl-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-1.3-dioxolane-4-carboxylate

methyl 2-((4R,5S)-5-((1R,2R,3R)-1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl)acetate

(4S,5R)-5-((1R,2R,3R)-1,3-Bis-benzyloxy-3-phenyl-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

1-[5-(1,3-bis(benzyloxy)-3-phenyl-2-(triisopropylsilanyloxy)propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-diazo-ethanone