methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate

Base Information

• Chemical Name: methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate
• CAS No.: 287934-47-8
• Molecular Formula: C₂₇H₃₈N₄O₁₃
• Molecular Weight: 626.618
• Mol file: 287934-47-8.mol

Synonyms:methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate

Chemical Property of methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate

There total 10 articles about methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-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:

methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate (295797-74-9) → methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate (287934-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-CaCO₃ / methanol / 2 h

2: 15.6 mg / DCC; HOBt / dimethylformamide / 0 - 20 °C

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; Lindlar's catalyst; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00999-1

Reference yield:

((N-(tert-butoxycarbonyl)glycyl)glycyl)glycine (28320-73-2) + (Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester (287934-39-8) → methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate (287934-47-8)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)00394-4

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) → methyl (Z)-2-[6'-(N-t-butoxycarbonylglycylglycylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenyl-acrylate (287934-47-8)

Guidance literature:

Multi-step reaction with 7 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: 78.6 mg / HOBt; DCC / dimethylformamide

With pyridine; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; 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;

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

upstream raw materials:

((N-(tert-butoxycarbonyl)glycyl)glycyl)glycine

(Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester

methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

(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