(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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester

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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester
• CAS No.: 419572-66-0
• Molecular Formula: C₃₅H₃₉NO₁₂S
• Molecular Weight: 697.76

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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester

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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester

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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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester

There total 6 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-(4-methoxy-benzyloxy)-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: 94.0%

2,2-dimethoxy-propane (77-76-9) + (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-[(3aR,4S,6S,6aS)-6-(1-Benzenesulfonyl-1-nitro-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-3-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester (419572-66-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 4h;

DOI:10.1002/1521-3765(20020104)8:1<293::AID-CHEM293>3.0.CO;2-L

Reference yield:

4-hydroxy-3-(4-methoxyphenylmethoxy)benzaldehyde (263887-24-7) → (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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester (419572-66-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / (1S,2S)-chx(o-NHCO-C₆H₄-PPh₂)2; Et₃N / [Pd₂dba3]*CHCl₃ / tetrahydrofuran / 1.5 h / 50 °C

2: 98 percent / N-methylmorpholine-N-oxide; aq. OsO₄ / CH₂Cl₂ / 20 °C

3: 100 percent / CH₂Cl₂ / 50 °C

4: 94 percent / p-TsOH / acetone / 4 h / 20 °C

With osmium(VIII) oxide; (1S,2S)-chx(o-NHCO-C₆H₄-PPh₂)2; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetone; 3: Wittig reaction;

DOI:10.1002/1521-3765(20020104)8:1<293::AID-CHEM293>3.0.CO;2-L

Reference yield:

benzoic (2SR,5SR)-5-(1-benzenesulfonyl-1-nitroethyl)-2,5-dihydrofuran-2-yl ester → (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-(4-methoxy-benzyloxy)-phenyl]-2-methyl-acrylic acid ethyl ester (419572-66-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / (1S,2S)-chx(o-NHCO-C₆H₄-PPh₂)2; Et₃N / [Pd₂dba3]*CHCl₃ / tetrahydrofuran / 1.5 h / 50 °C

2: 98 percent / N-methylmorpholine-N-oxide; aq. OsO₄ / CH₂Cl₂ / 20 °C

3: 100 percent / CH₂Cl₂ / 50 °C

4: 94 percent / p-TsOH / acetone / 4 h / 20 °C

With osmium(VIII) oxide; (1S,2S)-chx(o-NHCO-C₆H₄-PPh₂)2; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetone; 3: Wittig reaction;

DOI:10.1002/1521-3765(20020104)8:1<293::AID-CHEM293>3.0.CO;2-L

upstream raw materials:

2,2-dimethoxy-propane

(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

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-(4-methoxybenzyloxy)-phenyl}-2-methylacrylic acid

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