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

Base Information

• Chemical Name: methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate
• CAS No.: 478701-19-8
• Molecular Formula: C₄₀H₇₆O₉Si₄
• Molecular Weight: 813.38
• Mol file: 478701-19-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate 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: 81.0%

methyl (Z)-2-(6'-O-acetyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate (478701-12-1) → methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate (478701-19-8)

Guidance literature:

With sodium methylate; In methanol; at -20 ℃; for 1h;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate (481072-51-9) → methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate (478701-19-8)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate (864070-64-4) → methyl (Z)-2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate (478701-19-8)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

methyl (Z)-2-(6'-O-acetyl-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

Downstream raw materials:

(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