(E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene

Base Information

• Chemical Name: (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene
• CAS No.: 130034-69-4
• Molecular Formula: C₂₉H₄₂O₁₀Si
• Molecular Weight: 578.732
• Mol file: 130034-69-4.mol

Synonyms:(E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene

Chemical Property of (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene

There total 5 articles about (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene 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: 93.0%

tert-butyldimethylsilyl trifluoroacetate (104410-90-4) + (E)-4-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)but-3-en-2-one (130034-80-9) → (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene (130034-69-4)

Guidance literature:

With triethylamine; In dichloromethane; for 0.25h;

Reference yield:

6-O-benzyl-D-glucopyranose (20675-63-2,127753-65-5,127753-66-6) → (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene (130034-69-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / pyridine / 72 h

2: 89 percent / ammonia (g) / tetrahydrofuran; methanol / 0.75 h

3: 67 percent / thionyl chloride / dimethylformamide / 1.) 0 deg C, 1 h, 2.) room temperature, 16 h

4: 1.) silver(I) nitrate / 1.) 45 min, 2.) ethyl acetate, reflux, 24 h

5: 93 percent / triethylamine / CH₂Cl₂ / 0.25 h

With pyridine; thionyl chloride; ammonia; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

6-O-Benzyl-2,3,4-tri-O-acetyl-D-glucose (127753-67-7,127753-68-8) → (E)-1-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-3-(t-butyldimethylsiloxy)buta-1,3-diene (130034-69-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / thionyl chloride / dimethylformamide / 1.) 0 deg C, 1 h, 2.) room temperature, 16 h

2: 1.) silver(I) nitrate / 1.) 45 min, 2.) ethyl acetate, reflux, 24 h

3: 93 percent / triethylamine / CH₂Cl₂ / 0.25 h

With thionyl chloride; silver nitrate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyldimethylsilyl trifluoroacetate

(E)-4-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)but-3-en-2-one

6-O-benzyl-D-glucopyranose

6-O-Benzyl-2,3,4-tri-O-acetyl-α-D-glucopyranosyl chloride

Downstream raw materials:

(1S,2S,3R)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-5-(t-butyltrimethylsiloxy)-N-phenylcyclohex-4-ene-1,2-dicarboximide

(1R,2R,3S)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-5-(t-butyltrimethylsiloxy)-N-phenylcyclohex-4-ene-1,2-dicarboximide

(3S)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-5-(t-butyldimethylsiloxy)cyclohex-4-ene-1,1,2,2-tetracarbonitrile

(3R)-3-(6'-O-Benzyl-2',3',4'-tri-O-acetyl-α-D-glucopyranosyloxy)-5-(t-butyldimethylsiloxy)cyclohex-4-ene-1,1,2,2-tetracarbonitrile