(E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol

Base Information

• Chemical Name: (E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol
• CAS No.: 882048-19-3
• Molecular Formula: C₂₂H₃₆O₄Si
• Molecular Weight: 392.611

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

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

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

There total 1 articles about (E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol 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: 83.0%

(Z)-3-tributylstannyl-4-tetrahydro-2'H-pyran-2'-yl-2-buten-1,4-diol + [3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane (131362-25-9) → (E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol (882048-19-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In tetrahydrofuran; for 6h; Heating;

DOI:10.1021/ol060019s

Reference yield: 95.0%

(E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol (882048-19-3) + (Z)-2,2,2-trifluoro-N-(4-methoxyphenyl)acetimidoyl chloride (75999-66-5) → (E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-[(tetrahydro-2'H-pyran-2'-yl)oxy]-2-buten-1-yl N-(p-methoxyphenyl)-trifluoroacetimidate

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 5.5h;

DOI:10.1021/ol060019s

Reference yield: 83.0%

(E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-O-(tetrahydro-2'H-pyran-2'-yl)-2-buten-1,4-diol (882048-19-3) + trichloroacetonitrile (545-06-2) → (E)-3-(3'-tert-butyldimethylsilyloxy)-benzyl-4-[(tetrahydro-2'H-pyran-2'-yl)oxy]-2-buten-1-yl trichloroacetimidate

Guidance literature:

With sodium hydride; In diethyl ether; at 20 ℃; for 8h;

DOI:10.1021/ol060019s

upstream raw materials:

[3-(bromomethyl)-phenoxy]dimethyl(1,1-dimethylethyl)silane

Downstream raw materials:

3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

N-(p-methoxyphenyl)-O-(tetrahydro-2'H-pyran-2'-yl)-N-trifluoroacetyl-α-vinyl-m-tyrosinol

N-(p-methoxyphenyl)-O-(tetrahydro-2''H-pyran-2''-yl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

N-(9-fluorenylmethoxycarbonyl)-3'-O-triisopropylsilyl-α-vinyl-m-tyrosinol

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