Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

Base Information

• Chemical Name: Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate
• CAS No.: 139190-51-5
• Molecular Formula: C₃₀H₃₆O₅Si
• Molecular Weight: 504.698
• Mol file: 139190-51-5.mol

Synonyms:Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

Chemical Property of Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

There total 3 articles about Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate 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: 94.0%

Benzyloxymethyl chloride (3587-60-8) + Methyl (4S,E)-5-tert-butyldiphenylsiloxy-4-hydroxy-2-pentenoate (139190-68-4) → Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5)

Guidance literature:

With diisopropylamine; In dichloromethane; for 54h; Ambient temperature;

DOI:10.1055/s-1991-28396

Reference yield:

methyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate (81703-93-7) → Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5)

Guidance literature:

Multi-step reaction with 3 steps

1: AcOH / H₂O / 19 h / Ambient temperature

2: DMAP, imidazole / dimethylformamide / 16 h / Ambient temperature

3: 94 percent / i-Pr₂NH / CH₂Cl₂ / 54 h / Ambient temperature

With 1H-imidazole; dmap; acetic acid; diisopropylamine; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-1991-28396

Reference yield:

methyl (4S)‐4,5‐dihydroxypent‐2‐enoate (83541-54-2) → Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP, imidazole / dimethylformamide / 16 h / Ambient temperature

2: 94 percent / i-Pr₂NH / CH₂Cl₂ / 54 h / Ambient temperature

With 1H-imidazole; dmap; diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1991-28396

upstream raw materials:

Benzyloxymethyl chloride

Methyl (4S,E)-5-tert-butyldiphenylsiloxy-4-hydroxy-2-pentenoate

methyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

methyl (4S)‐4,5‐dihydroxypent‐2‐enoate

Downstream raw materials:

Methyl (3R,4S)-4-(benzyloxymethoxy)-5-tert-butyldiphenylsiloxy-3-methylpentanoate

(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

(3R,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-phenyl-pentanoic acid methyl ester

(3S,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentan-1-ol