(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

Base Information

• Chemical Name: (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
• CAS No.: 394738-15-9
• Molecular Formula: C₂₅H₂₇NO₁₁S
• Molecular Weight: 549.555

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 9 articles about (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 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-[(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 (394738-20-6) → (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 (394738-15-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; 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-[(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 (394738-15-9)

Guidance literature:

Multi-step reaction with 6 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

5: 95 percent / p-TsOH / CH₂Cl₂ / 20 °C

6: 100 percent / LiOH / methanol; H₂O; tetrahydrofuran / 50 °C

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

DOI:10.1002/1521-3773(20011001)40

Reference yield:

1-phenylsulfonyl-1-nitroethane sodium salt → (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 (394738-15-9)

Guidance literature:

Multi-step reaction with 7 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

6: 95 percent / p-TsOH / CH₂Cl₂ / 20 °C

7: 100 percent / LiOH / methanol; H₂O; tetrahydrofuran / 50 °C

With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); lithium hydroxide; 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-[(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

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

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

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

Downstream raw materials:

(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

C-2-epi-hygromycin A

(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

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