(E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol

Base Information

• Chemical Name: (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol
• CAS No.: 882048-23-9
• Molecular Formula: C₂₈H₅₀O₅Si₂
• Molecular Weight: 522.873

Synonyms:(E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol

Chemical Property of (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol

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Technology Process of (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol

There total 3 articles about (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol 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: 90.0%

(E)-ethyl 3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-butenoate (882048-37-5) → (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol (882048-23-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 - 20 ℃; for 6h;

DOI:10.1021/ol060019s

Reference yield:

(Z)-ethyl 3-tributylstannyl-4-[(tetrahydro-2'H-pyran-2'-yl)oxy]-crotonate → (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol (882048-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / triphenylarsine; Pd₂dba3 / tetrahydrofuran / Heating

2: 90 percent / diisobutylaluminum hydride / tetrahydrofuran / 6 h / -78 - 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; diisobutylaluminium hydride; In tetrahydrofuran; 1: Stille coupling;

DOI:10.1021/ol060019s

Reference yield:

4-bromomethyl-1,2-bis(tert-butyl-dimethyl-silanyloxy)benzene (161688-42-2) → (E)-3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-buten-1-ol (882048-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / triphenylarsine; Pd₂dba3 / tetrahydrofuran / Heating

2: 90 percent / diisobutylaluminum hydride / tetrahydrofuran / 6 h / -78 - 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; diisobutylaluminium hydride; In tetrahydrofuran; 1: Stille coupling;

DOI:10.1021/ol060019s

upstream raw materials:

(E)-ethyl 3-(3',4'-di-tert-butyldimethylsilyloxy)benzyl-4-(tetrahydro-2'H-pyran-2'-yl)oxy-2-butenoate

4-bromomethyl-1,2-bis(tert-butyl-dimethyl-silanyloxy)benzene

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