(E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester
• CAS No.: 394738-19-3
• Molecular Formula: C₂₄H₂₇NO₁₁S
• Molecular Weight: 537.544

Synonyms:(E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester

Chemical Property of (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester

Chemical Property:

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Technology Process of (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester

There total 8 articles about (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl 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: 100.0%

(E)-3-{4-[(2S,3R,4S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-3,4-dihydroxy-tetrahydrofuran-2-yloxy]-3-(4-methoxybenzyloxy)-phenyl}-2-methylacrylic ethyl ester (394738-14-8) → (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester (394738-19-3)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; at 50 ℃;

DOI:10.1002/1521-3773(20011001)40

Reference yield:

benzoic (2S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-2,5-dihydrofuran-2-yl ester (394738-12-6) → (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester (394738-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / (S,S)-1,2-bis(o-Ph₂P-C₆H₄-CO-NH)-cyclohexane; Et₃N / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 50 °C

2: 98 percent / OsO₄; NMO / CH₂Cl₂ / 20 °C

3: 99 percent / CH₂Cl₂ / 45 °C

4: 100 percent / p-TsOH / methanol; tetrahydrofuran / 50 °C

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); osmium(VIII) oxide; N-methyl-2-indolinone; toluene-4-sulfonic acid; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; methanol; dichloromethane; 3: wittig reaction;

DOI:10.1002/1521-3773(20011001)40

Reference yield:

1-phenylsulfonyl-1-nitroethane sodium salt → (E)-3-{4-[(2S,3R,4S,5S)-5-(1-Benzenesulfonyl-1-nitro-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid ethyl ester (394738-19-3)

Guidance literature:

Multi-step reaction with 5 steps

1: (R,R)-1,2-bis(o-Ph2P-C6H4-CO-NH)-cyclohexane; (n-C6H13)4NBr / {η³-C3H5PdCl}2 / CH2Cl2; H2O / 20 °C

2: 75 percent / (S,S)-1,2-bis(o-Ph₂P-C₆H₄-CO-NH)-cyclohexane; Et₃N / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 50 °C

3: 98 percent / OsO₄; NMO / CH₂Cl₂ / 20 °C

4: 99 percent / CH₂Cl₂ / 45 °C

5: 100 percent / p-TsOH / methanol; tetrahydrofuran / 50 °C

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); osmium(VIII) oxide; N-methyl-2-indolinone; tetrahexylammonium bromide; toluene-4-sulfonic acid; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; methanol; dichloromethane; water; 4: wittig reaction;

DOI:10.1002/1521-3773(20011001)40

upstream raw materials:

(E)-3-{4-[(2S,3R,4S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-3,4-dihydroxy-tetrahydrofuran-2-yloxy]-3-(4-methoxybenzyloxy)-phenyl}-2-methylacrylic ethyl ester

(carbethoxyethylidene)triphenylphosphorane

4-hydroxy-3-(4-methoxyphenylmethoxy)benzaldehyde

4-[(2S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-2,5-dihydrofuran-2-yloxy]-3-(4-methoxybenzyloxy)-benzaldehyde

Downstream raw materials:

(E)-3-{4-[(3aR,4S,6S,6aR)-6-(1-benzenesulfonyl-1-nitroethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic ethyl ester

(E)-3-{4-[(3aR,4S,6S,6aR)-6-acetyl-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

(E)-3-{4-[(3aR,4S,6S,6aR)-2,2-dimethyl-6-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydrofuro[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxyphenyl}-2-methylacrylic acid

(E)-3-{4-[(3aR,4S,6S,6aS)-6-(1-Benzenesulfonyl-1-nitro-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-3-hydroxy-phenyl}-2-methyl-acrylic acid

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