(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

Base Information

Chemical Name:(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
CAS No.:287934-39-8
Molecular Formula:C₁₆H₂₁NO₈
Molecular Weight:355.345
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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:

: 295797-74-9
methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

: 287934-39-8
(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

Guidance literature:: With hydrogen; Lindlar's catalyst;
DOI:10.1016/S0040-4039(00)00394-4

Reference yield:

: 295797-77-2
(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

: 287934-39-8
(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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Tosylation / 2: Acetylation / 3: Substitution / 4: Substitution / 5: Deacetylation / 6: Catalytic hydrogenation;
DOI:10.1016/S0040-4020(00)00421-X

Reference yield:

: 295797-73-8
methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

: 287934-39-8
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / NaOMe / methanol / 0.5 h

2: H₂ / Pd-CaCO₃ / methanol / 4 h

With hydrogen; sodium methylate; Lindlar's catalyst; In methanol; 1: Deacetylation / 2: Catalytic hydrogenation;
DOI:10.1016/S0040-4020(00)00421-X