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

Base Information

• Chemical Name: (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester
• CAS No.: 295797-77-2
• Molecular Formula: C₂₂H₃₄O₉Si
• Molecular Weight: 470.592
• Mol file: 295797-77-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-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: 86.0%

(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester (223930-89-0) → (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester (295797-77-2)

Guidance literature:

With sodium methylate; In methanol; for 3h;

DOI:10.1016/S0040-4020(00)00421-X

Reference yield: 67.0%

p-toluenesulfonyl chloride (98-59-9) + (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester (295797-77-2) → (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-acrylic acid methyl ester (295797-78-3)

Guidance literature:

With pyridine; at 20 ℃; for 5h;

DOI:10.1016/S0040-4020(00)00421-X

Reference yield:

(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester (295797-77-2) → (Z)-2-{(2S,3R,4S,5R,6R)-6-[(2-Amino-acetylamino)-methyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy}-3-(4-hydroxy-phenyl)-acrylic acid methyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: 67 percent / pyridine / 5 h / 20 °C

2: 100 percent / pyridine / 20 °C

3: 100 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

4: 63 percent / NaN₃; 15-crown-5 / dimethylformamide / 48 h / 70 °C

5: 84 percent / NaOMe / methanol / 0.5 h

6: H₂ / Pd-CaCO₃ / methanol / 4 h

7: 10.3 mg / WSC / dimethylformamide / 20 °C

8: H₂ / Pearlman's catalyst / methanol / 2 h

With pyridine; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Tosylation / 2: Acetylation / 3: Substitution / 4: Substitution / 5: Deacetylation / 6: Catalytic hydrogenation / 7: Acylation / 8: Hydrogenolysis;

DOI:10.1016/S0040-4020(00)00421-X

upstream raw materials:

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

Downstream raw materials:

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

methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate

(R)-3-(4-Hydroxy-phenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-propionic acid methyl ester