(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester
• CAS No.: 478701-13-2
• Molecular Formula: C₄₀H₇₄O₉Si₄
• Molecular Weight: 811.364

Synonyms:(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester

Chemical Property of (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester

There total 13 articles about (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl 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: 60.0%

methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate (478701-19-8) → (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester (478701-13-2)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; for 1h;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate (481072-51-9) → (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester (478701-13-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / pyridine

2: 98 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran

3: AgOTf / molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / -30 - 20 °C

4: sodium methoxide / methanol / 7 h / 20 °C

5: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6: hydrogen / Pd(OH)2 / tetrahydrofuran

7: pyridine

8: 76.0 mg / 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 24 h / Heating

9: 81 percent / sodium methoxide / methanol / 1 h / -20 °C

10: 60 percent / SO₃*pyridine; triethylamine / dimethylsulfoxide / 1 h

With pyridine; 2,6-dimethylpyridine; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silver trifluoromethanesulfonate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate (864070-64-4) → (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5S,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-formyl-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester (478701-13-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran

2: AgOTf / molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / -30 - 20 °C

3: sodium methoxide / methanol / 7 h / 20 °C

4: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5: hydrogen / Pd(OH)2 / tetrahydrofuran

6: pyridine

7: 76.0 mg / 2,3-dichloro-5,6-dicyano-p-benzoquinone / dioxane / 24 h / Heating

8: 81 percent / sodium methoxide / methanol / 1 h / -20 °C

9: 60 percent / SO₃*pyridine; triethylamine / dimethylsulfoxide / 1 h

With pyridine; 2,6-dimethylpyridine; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silver trifluoromethanesulfonate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate

methyl 3-p-benzyloxyphenyl-2-t-butyldimethylsiloxy propionate

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